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4-Amino-5-chloro-N-(2-(diethylamino)ethyl)-2-methoxybenzamide

4-Amino-5-chloro-N-(2-(diethylamino)ethyl)-2-methoxybenzamide structure

CAS No.: 364-62-5

Chemical Name:: 4-Amino-5-chloro-N-(2-(diethylamino)ethyl)-2-methoxybenzamide

Synonyms: Metoclopramide;DEL;Metaclopramide;Primperan;Metochlopramide;C07868;Parmid;Plasil;del1267;DEL 1267

CBNumber:: CB4506227

Molecular Formula:: C14H22ClN3O2

Molecular Weight:: 299.8

MDL Number:: MFCD00211338

MOL File:: 364-62-5.mol

Last updated:2024-11-19 23:02:33

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4-Amino-5-chloro-N-(2-(diethylamino)ethyl)-2-methoxybenzamide Properties

Melting point	146-148°C
Boiling point	418.7±45.0 °C(Predicted)
Density	1.2432 (rough estimate)
refractive index	1.5200 (estimate)
storage temp.	2-8°C
solubility	Practically insoluble in water, sparingly soluble or slightly soluble in ethanol (96 per cent), slightly soluble in methylene chloride
form	Solid
pka	pKa 0.42± 0.03;9.71± 0.02(H2O)(Approximate)
color	White to Off-White
BRN	1884366
CAS DataBase Reference	364-62-5(CAS DataBase Reference)
NCI Dictionary of Cancer Terms	metoclopramide
FDA UNII	L4YEB44I46
ATC code	A03FA01
NIST Chemistry Reference	Benzamide, 4-amino-5-chloro-n-[2-(diethylamino)ethyl]-2-methoxy-(364-62-5)

SAFETY

Risk and Safety Statements

Symbol(GHS)

GHS07

Signal word

Warning

Hazard statements

H302

Precautionary statements

P264-P270-P301+P312-P501

Hazard Codes

Risk Statements

22-64

Safety Statements

36/37

WGK Germany

HS Code

2924.29.7790

NFPA 704

	0
2		0

4-Amino-5-chloro-N-(2-(diethylamino)ethyl)-2-methoxybenzamide price More Price(20)

Manufacturer	Product number	Product description	CAS number	Packaging	Price	Updated	Buy
Sigma-Aldrich	M1824990	Metoclopramide European Pharmacopoeia (EP) Reference Standard	364-62-5	m1824990	$220	2024-03-01	Buy
Sigma-Aldrich	32473	Metoclopramide VETRANAL	364-62-5	100mg	$140	2024-03-01	Buy
TRC	M338698	Metoclopramide	364-62-5	1g	$65	2021-12-16	Buy
AK Scientific	H780	Metoclopramide	364-62-5	100mg	$72	2021-12-16	Buy
AK Scientific	H780	Metoclopramide	364-62-5	1g	$144	2021-12-16	Buy

Product number	Packaging	Price	Buy
M1824990	m1824990	$220	Buy
32473	100mg	$140	Buy
M338698	1g	$65	Buy
H780	100mg	$72	Buy
H780	1g	$144	Buy

4-Amino-5-chloro-N-(2-(diethylamino)ethyl)-2-methoxybenzamide Chemical Properties,Uses,Production

Uses

Metoclopramide is a treatment of choice of post-operative nausea and vomiting (PONV) prophylaxis.

Chemical Properties

White or almost white, fine powder.

Originator

Primperan,Delagrange,France,1964

Uses

Metoclopramide is a treatment of choice of post-operative nausea and vomiting (PONV) prophylaxis.

Uses

antidiabetic

Definition

ChEBI: A member of the class of benzamides resulting from the formal condensation of 4-amino-5-chloro-2-methoxybenzoic acid with the primary amino group of N,N-diethylethane-1,2-diamine.

Manufacturing Process

The N-(diethylaminoethyl)-2-methoxy-4-aminobenzamide used as the starting material may be prepared from o-toluidine. The o-toluidine is initially nitrated with nitric acid to produce 4-nitro-o-toluidine. The 4-nitro-o-toluidine is then converted to 2-hydroxy-4-nitrotoluene by heating with nitrous acid. By reacting the resulting 2-hydroxy-4-nitrotoluene with dimethyl sulfate, 2- methoxy-4-nitrotoluene is formed. The 2-methoxy-4-nitrotoluene is oxidized with potassium permanganate to produce 2-methoxy-4-nitrobenzoic acid. The latter substituted benzoic acid is treated with thionyl chloride to form 2- methoxy-4-nitrobenzoyl chloride. A methyl ethyl ketone solution of the 2- methoxy-4-nitrobenzoyl chloride is added over a period of about 1? hours to a methyl ethyl ketone solution containing an equal molecular quantity of N,Ndiethylethylene diamine while stirring and maintaining the temperature between 0°C and 5°C. The N-(diethylaminoethyl)-2-methoxy-4- nitrobenzamide hydrochloride formed precipitates. It is filtered, washed twice with methyl ethyl ketone, dissolved in alcohol, and reduced catalytically in an absolute isopropyl alcohol solution to form N-(diethylaminoethyl)-2-methoxy- 4-aminobenzamide. The base is obtained by precipitating with sodium hydroxide.
80 g (0.3mol) of N-(2-diethylaminoethyl)-2-methoxy-4-aminobenzamide are dissolved in small portions in 150 cc of acetic acid. The mixture is cooled and 45 g (0.45 mol) of acetic anhydride are added, and the solution obtained is heated for two hours on a water bath. After cooling, the solution is decanted into a round-bottomed flask with a stirrer, a thermometer and a tube for introducing the chlorine. It is stirred and the current of chlorine is passed through, the temperature being maintained between 20°C and 25°C. The stirring is continued for one hour after the completion of the absorption of the chlorine.
The mixture obtained is poured into 2 liters of water and the base is precipitated with 30% soda. The precipitated base is extracted with 400 cc of methylene chloride. After evaporation of the solvent, the N-(2- diethylaminoethyl)-2-methoxy-4-acetamino-5-chlorobenzamide formed crystallizes. The melting point is 86°C to 87°C and the yield is 95%.
To obtain the corresponding amino derivative, 109 g of base are heated under agitation in a round-bottomed flask with 300 cc of 35-36% concentrated hydrochloric acid and 600 cc of water. It is heated on a water bath until dissolution is complete, then maintained at boiling point for 90 minutes, cooled, diluted with 1 liter of water, and neutralized with about 350 cc of 30% soda. The N-(2-diethylaminoethyl)-2-methoxy-4-amino-5-chlorobenzamide formed crystallizes, is centrifuged and washed in water. Its melting point is 122°C and the yield is 74%.
To obtain the corresponding dihydrochloride, the base is dissolved in absolute alcohol (3 volumes) and to that solution is added 5 N alcoholic hydrochloric acid. The dihydrochloride precipitates, is centrifuged and washed with alcohol. It is a solid white material, having a melting point of 134°C to 135°C.

brand name

Maxolon (King); Reglan (Baxter Healthcare); Reglan (Robins); Reglan (Schwarz Pharma).

Therapeutic Function

Antiemetic

General Description

Metoclopramide is typically employed as an antiemetic drug or a gastrointestinal prokinetic drug in adults and children.

4-Amino-5-chloro-N-(2-(diethylamino)ethyl)-2-methoxybenzamide synthesis

Synthesis of 4-Amino-5-chloro-N-(2-(diethylamino)ethyl)-2-methoxybenzamide from METOCLOPRAMIDE HCL

4-Amino-5-chloro-N-(2-(diethylamino)ethyl)-2-methoxybenzamide Preparation Products And Raw materials

Raw materials

Ammonium chloride METHYL 4-AMINOSALICYLATE Chlorine

Preparation Products

N-Desethyl MetoclopraMide

4-Amino-5-chloro-N-(2-(diethylamino)ethyl)-2-methoxybenzamide Suppliers

Global( 307)Suppliers

Supplier	Tel	Email	Country	ProdList	Advantage
Shaanxi Dideu Medichem Co. Ltd	+86-029-81138252 +86-18789408387	1057@dideu.com	China	3958	58
Changzhou Rokechem Technology Co., Ltd.	18758118018	sales001@rokechem.com	China	255	58
shandong perfect biotechnology co.ltd	+86-53169958659 +86-13153181156	sales@sdperfect.com	China	294	58
Guangzhou Tengyue Chemical Co., Ltd.	+86-86-18148706580 +8618826483838	evan@tyvovo.com	China	148	58
Hebei Xinsheng New Material Technology Co., LTD.	+86-16632316109	xinshengkeji@xsmaterial.com	China	1085	58
Apeloa production Co.,Limited	+8619933239880	admin@apcl.com.cn	China	852	58
Hebei Ganmiao New material Technology Co., LTD	+86-17332992504 +86-17332992504	sales8@hbganmiao.com	China	299	58
BEIJING SJAR TECHNOLOGY DEVELOPMENT CO., LTD.	+86-18600796368 +86-18600796368	sales@sjar-tech.com	China	444	58
Shanghai Daken Advanced Materials Co.,Ltd	+86-371-66670886	info@dakenam.com	China	18775	58
ATK CHEMICAL COMPANY LIMITED	+undefined-21-51877795	ivan@atkchemical.com	China	32957	60

Supplier	Advantage
Shaanxi Dideu Medichem Co. Ltd	58
Changzhou Rokechem Technology Co., Ltd.	58
shandong perfect biotechnology co.ltd	58
Guangzhou Tengyue Chemical Co., Ltd.	58
Hebei Xinsheng New Material Technology Co., LTD.	58
Apeloa production Co.,Limited	58
Hebei Ganmiao New material Technology Co., LTD	58
BEIJING SJAR TECHNOLOGY DEVELOPMENT CO., LTD.	58
Shanghai Daken Advanced Materials Co.,Ltd	58
ATK CHEMICAL COMPANY LIMITED	60

View Lastest Price from 4-Amino-5-chloro-N-(2-(diethylamino)ethyl)-2-methoxybenzamide manufacturers

Update time	Product	Price	Min. Order	Purity	Supply Ability	Manufacturer
2024-11-27	Metoclopramide 364-62-5	US $0.00-0.00 / Kg/Drum	1KG	99%min	1000kg	WUHAN FORTUNA CHEMICAL CO., LTD
2024-11-19	Metoclopramide 364-62-5	US $55.00-125.00 / mg		99.81%	10g	TargetMol Chemicals Inc.
2024-11-19	metoclopramide 364-62-5	US $1.00 / g	1g	0.98	1000	Apeloa production Co.,Limited

Metoclopramide
364-62-5
US $0.00-0.00 / Kg/Drum
99%min
WUHAN FORTUNA CHEMICAL CO., LTD

Metoclopramide
364-62-5
US $55.00-125.00 / mg
99.81%
TargetMol Chemicals Inc.

metoclopramide
364-62-5
US $1.00 / g
0.98
Apeloa production Co.,Limited

4-Amino-5-chloro-N-(2-(diethylamino)ethyl)-2-methoxybenzamide Spectrum

4-Amino-5-chloro-N-(2-(diethylamino)ethyl)-2-methoxybenzamide(364-62-5)¹HNMR

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4-amino-5-chloro-N-[2-(diethylamino)ethyl]-2-methoxybenzamide monohydrochloride 2-METHOXY-D3-BENZALDEHYDE 4-amino-5-chloro-N-[2-(diethylamino)ethyl]-2-methoxybenzamide dihydrochloride

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4-amino-5-chloro-n-(2-(diethylamino)ethyl)-n-anisamid Methoxychloroprocainamide Methoxychlorprocainamide 4-Amino-5-chloro-N-(2-diethylamino) ethyl-o-anisamide Benzamide, 4-amino-5-chloro-N-2-(diethylamino)ethyl-2-methoxy- Metoclopramide (base and/or unspecified salts) 4-Amino-5-chloro-N-(2-(diethylamino)ethyl)-2-methoxybenzamide 4-Amino-5-Cholo-N-[(2-diethylamino)ethyl]-2-methyloxy- C07868 4-amino-5-chloro-n-(2-(diethylamino)ethyl)-o-anisamid 4-Amino-5-Cholo-N-[(2-diethylamino)ethyl]-2-methyloxy-benzamide 2-Methoxy-5-Chloroprocainamide 4-amino-5-chloro-n-(2-(diethylamino)ethyl)-2-methoxy-benzamid 5-Chloro-2-methoxyprocainamide Anisamide, 4-amino-5-chloro-N-(2-(diethylamino)ethyl)- DEL 1267 del1267 Metaclopromide Methochlopramide Methoclopramide Metoclol Metoclopranide Metocobil Metramid Moriperan N-(Diethylaminoethyl)-2-methoxy-4-amino-5-chlorobenzamide o-Anisamide, 4-amino-5-chloro-N-[2-(diethylamino)ethyl]- Parmid Plasil Reliveran Metoclopramide CRS Metoclopramide Standard Metoclopramide> 4-amino-5-chloro-N - (2- (diethylamino) ethyl) -2-methoxybenzoamide 4-Amino-5-chloro-N-(2-(diethylamino)ethyl)-2-methoxybenzamide USP/EP/BP 5-Trimethoxyphenylacrylic acid 5-Trimethoxy-trans-cinnamic acid Metoclopramide DEL Metaclopramide Metochlopramide Primperan Amine chloride tome Metoclopramide, 4-Amino-5-chloro-N-(2-(diethylamino)ethyl)-2-methoxybenzamide Metoclopramide B.P. /Ph.Eur 364-62-5 PRANDIN API 364-62-5