반응 #2456053

반응 방정식

3-(ethoxycarbonyl)-5-nitrobenzoic acid

→

3-amino-5-(ethoxycarbonyl)benzoic acid

용매

MeOH

반응 조건

후처리

1. 1
   여과the mixture was filtered through Celite
2. 2
   농축concentrated

실험 절차

A mixture of 3-(ethoxycarbonyl)-5-nitrobenzoic acid (5 g, 20.905 mmol) and 10% Pd/C (1.11 g, 1.045 mmol) in 100 mL of MeOH was stirred under H2 gas at room temperature. After 4 hours, the mixture was filtered through Celite and concentrated to give 3-amino-5-(ethoxycarbonyl)benzoic acid. To a solution of 3-amino-5-(ethoxycarbonyl)benzoic acid (2 g, 9.56 mmol) in 10 mL of DMF was added formaldehyde (about 37% wt % in H2O, 7.118 mL, 95.60 mmol) at room temperature. After 10 minutes, the solution was cooled to 0° C. and NaBH3CN (1.897 g, 28.68 mmol) was added. The mixture was stirred at room temperature for 3 hours. The solution was diluted with EtOAc. The solution was washed with 5% citric acid and saturated brine and dried with Na2SO4. The solution was filtered and concentrated to give 3-(Dimethylamino)-5-(ethoxycarbonyl)benzoic acid Compound 1 (2.1 g, 92% in two steps). 1H-NMR (500 MHz, DMSO-d6) δ 7.78 (s, 1H), 7.44 (s, 1H), 7.41 (s, 1H), 4.32 (q, J=7.1 Hz, 2H), 2.99 (s, 6H), 1.33 (t, J=7.1 Hz, 3H); 13C-NMR (125 MHz, DMSO-d6) δ 166.99, 165.54, 150.14, 131.76, 130.79, 116.89, 116.25, 115.59, 60.79, 39.84, 14.05; ESI-MS: m/z (MH+): 238.1074 (calc'd), 238.1076 (found).

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