(4-Amino-3-chloro-phenyl)-acetic acid methyl ester synthesis

7synthesis methods

Product Name:(4-Amino-3-chloro-phenyl)-acetic acid methyl ester
CAS Number:101349-30-8
Molecular formula:C9H10ClNO2
Molecular Weight:199.63

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Benzeneacetic acid, 3-chloro-4-nitro-, methyl ester

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(4-Amino-3-chloro-phenyl)-acetic acid methyl ester

101349-30-8
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Yield: 48%

Reaction Conditions:

with acetic acid in methanol;water

Steps:

84 4-[1-[3-chloro-4-[1N'-(2-methylphenyl)ureido]phenylacetyl]-(4S)-fluoro-(2S)-pyrrolidinyl]methoxybenzoic Acid
A mixture of methyl 3chloro-4-nitrophenylacetate (10.9 g, 47.5 mmol), reduced iron powder (8.58 g, 153.6 mmol), AcONa.3H₂O (6.05 g, 44.5 mmol) and AcOH (17.6 ml) in MeOH/H₂O (100/400 ml) was heated at 110° C. for 1 h. After cooled to room temperature, the reaction mixture was filtered through Celite and the filtered cake was washed with MeOH. The combined filtrate were evaporated and extracted with EtOAc. The combined extracts were washed with brine, dried over Na₂SO₄ and concentrated in vacuo. The residue was chromatographed on silica gel [150 g, CHCl₃₁EtOAc (10/1)] to give methyl 4-amino-3-chlorophenylacetate (4.58 g, 48%) as a red oil. ¹H-NMR (CDCl₃) δ 3.49 (s, 2H), 3.68 (s, 3H), 4.01 (br, 2H), 6.70 (d, J=7.4 Hz, 1H), 6.96 (dd, J=8.1, 2.0 Hz, 1H), 7.17 (d, J=2.0 Hz, 1H).

References:

Daiichi Pharmaceutical Co., LTD. US2003/78249, 2003, A1

67-56-1 Synthesis