Methyl 2-amino-5-(3-chloropropoxy)-4-Methoxybenzoate synthesis

5synthesis methods

Product Name:Methyl 2-amino-5-(3-chloropropoxy)-4-Methoxybenzoate
CAS Number:380844-26-8
Molecular formula:C12H16ClNO4
Molecular Weight:273.71

methyl 5-(3-chloropropoxy)-4-methoxy-2-nitrobenzoate

380844-24-6
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Methyl 2-amino-5-(3-chloropropoxy)-4-Methoxybenzoate

380844-26-8
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Yield:380844-26-8 98.1%

Reaction Conditions:

with hydrogen;palladium on activated carbon in methanol;water at 40; under 760.051 Torr; for 2 h;

Steps:

III-11 [Example III-11] Preparation of methyl 4-methoxy-5-(3-chloropropoxy) anthranilate

In a 50 mL volume glass flask equipped with a stirrer, a thermometer, a reflux condenser and a gas inlet were placed 2.02 g (6.58 mmol) of methyl 4-methoxy-5-(3-chloropropoxy)-2-nitrobenzoate (purity: 99%) obtained in Reference Example III-12, and 40 mL of methanol. The resulting mixture was heated to 40°C under stirring. To the mixture was added 0.2 g of 5 wt.% palladium/carbon (containing 49% water) at the same temperature. The resulting mixture was heated to the same temperature for 2 hours, while hydrogen was introduced into the mixture under atmospheric pressure at a rate of 50 mL/min. After the reaction was complete, the reaction mixture was filtered and the filtrate was concentrated under reduced pressure, to precipitate a crystalline product. The crystalline product was dried under reduced pressure, to give 1.80 g (isolated yield: 98.1%, purity: 98% in terms of area percentage determined by high performance liquid chromatography) of methyl 4-methoxy-5-(3-chloropropoxy)anthranilate as a white crystalline product. Methyl 4-methoxy-5-(3-chloropropoxy)anthranilate had the following characteristics. m.p.: 92-93°C 1H-NMR (CDCl3, δ (ppm)): 2.19-2.27 (2H, m), 2.73-2.76 (2H, m), 3.80 (3H, s), 3.84 (3H, s), 4.09 (2H, t, J=6.0Hz), 5.59 (2H, brs), 6.13 (1H, s), 7.37 (1H, s)

References:

EP1477481,2004,A1 Location in patent:Page 31