ChemicalBook CAS DataBase List 2-chloro-4-ethoxybenzenaMine

2-chloro-4-ethoxybenzenaMine synthesis

8synthesis methods

Product Name:2-chloro-4-ethoxybenzenaMine
CAS Number:178452-11-4
Molecular formula:C8H10ClNO
Molecular Weight:171.62

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Yield:178452-11-4 41%

Reaction Conditions:

with potassium carbonate in N,N-dimethyl-formamide at 20; for 20 h;

Steps:

a) 2-Chloro-4-ethoxyaniline

K2003 (3.89 g, 28.15 mmol) and ethyl iodide (0.99 mL, 12.40 mmol) were added to a suspension of 4-amino-3-chlorophenol hydrochloride (2.03 g, 11.28 mmol)in DMF (25 mL). The resulting suspension was stirred at rt for 20 h. After removal of volatiles by rotatory evaporation, the residue was diluted with EtOAc (80 mL) and was washed with water (60 mL). The aqueous phase was extracted with EtOAc (3x30 mL), the combined organic layers were dried over Na2SO4 (anhydrous), filtered and concentrated. The crude residue was purified by flashchromatography on Si02 (10-30% EtOAc/hexanes) to afford 2-chloro-4- ethoxyaniline (reddish oil, 0.77 g, 41% yield).HPLC-MS (Method B): Ret, 9.39 mm; ESl-MS mlz: 172 (M+1).

References:

WO2018/1973,2018,A1 Location in patent:Page/Page column 197

5391-55-9 Synthesis