2-Amino-4-chlorobenzamide

To a solution of 2-amino-4-chlorobenzoic acid 11 (3.4 g, 20 mmol) and HOBt (3.0 g, 22 mmol) in DMF (50 mL) was addedEDCI (4.6 g, 24 mmol). The mixture was stirred at rt for 2 h. Theresulting solution was cooled to 0 °C, then 25percent ammonia solution(20 mL) was added. The mixture was warmed to ambient temperatureand stirred for 1 h. The reaction mixture was poured intocrushed ice, filtered and washed with water to give 12 (3.0 g, 88percentyield) as gray solid. 1H NMR (400 MHz, DMSO‑d6) δ: 7.77 (s, 1H), 7.54 (d, J = 8.5 Hz, 1H), 7.14 (s, 1H), 6.82 (s, 2H), 6.74 (d, J = 2.1 Hz, 1H), 6.49 (dd, J = 8.5, 2.1 Hz, 1H). 13C NMR (101 MHz, DMSO‑d6) δ:170.90, 151.98, 136.78, 131.06, 115.55, 114.45, 112.86 ppm. MS(ESI APCI) m/z 171.0 [M+H]+.Method I: 2-Amino-4-chlorobenzamide (ii-b) HOBt (2.70 g, 20 mmol) was added to a mixture of 2-amino-4-chlorobenzoic acid (3.42 g, 20 mmol) in DMF (45 mL).After stirring for 10 minutes, EDC hydrogen chloride (3.82 g, 20 mmol) was added to the mixture. The resulting mixture was stirred at room temperature for 2 hours.NH 4 OH (28percent, 5 mL) was added at 0 ° C. with vigorous stirring.After the addition, the mixture was stirred at room temperature for a further 2 hours.The reaction mixture was added dropwise to water (200 mL) with stirring, and a precipitate was formed. The precipitate was collected and dried in vacuo to give 2.98 g of ii-b as a gray solid (yield 87.6percent).[00393] Step A: To solution of 2-amino-4-chlorobenzoic acid (4.4 g, 25.8 mmol) in degassed DMF (75 mL) were added successively HOBt (4.19 g, 31 mmol), DIEA (5.4 mL, 31 mmol), EDCI (5.37 g, 28 mmol), and 2N NHStep A:Reference 2-amino-4-chlorobenzamide

Molecular Weight:170.59
XLogP3:0.9
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:1
Exact Mass:170.0246905
Monoisotopic Mass:170.0246905
Topological Polar Surface Area:69.1
Heavy Atom Count:11
Complexity:163
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes