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659-04-1 Synthesis

659-04-1
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58186-45-1
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Yield:58186-45-1 100%

Reaction Conditions:

with stannous chloride in methanol at 65; for 2 h;

Steps:

2 Step 2: (￡)-Methyl 3-(3-aminophenyl)acrylate

Step 2: (￡)-Methyl 3-(3-aminophenyl)acrylate [00393] A suspension of (￡)-methyl 3-(3-nitrophenyl)acrylate (1.95 g, 9.40 mmol), tin (II) chloride dihydrate (7.20 g, 31.9 mmol), and methanol (27 mL) was heated at 65 °C for 2 h, cooled to room temperature, and poured into ice water (100 mL). The reaction mixture was diluted with saturated NaHC0₃ (200 mL) and extracted with ethyl acetate (3 x400 mL). The organic extracts were washed (200 mL brine), dried (Na₂S0₄), and concentrated under reduced pressure to give (￡)-methyl 3-(3-aminophenyl)acrylate (1.68 g, 100%) as yellow solid. ¹H MR (400 MHz, DMSO-i): δ 7.48 (d, J= 15.8 Hz, 1H), 7.06 (t, J= 7.8 Hz, 1H), 6.85-6.79 (m, 2H), 6.65-6.61 (m, 1H), 6.41 (d, J= 15.8 Hz, 1H), 5.19 (s, 2H), 3.71 (s, 3H).

References:

WO2017/49172,2017,A1 Location in patent:Paragraph 00393

99-61-6 Synthesis