3-AMINOBENZOYLMETHYLAMIDE

A mixture of N-methyl-3-nitro-benzamide (2.47 g, 13.71 mmol) and 10percent Pd/C (0.5 g) in methanol (50 ML) was hydrogenated at room temperature and atmospheric pressure overnight.The reaction mixture was filtered through a Celite pad and concentrated.The crude material was used in the next step without further purification. (Yield 2.06 g, 100percent). Step 3 [00509] Intermediate 48: 3-amino-N-methyl-benzamide[00510] A solution of ethyl 3-aminobenzoate (0.l8mL, 1.21 mmol), methylamine (0.44mL, 12.llmmol) and sodium methoxide (6mg, 0.O3mmol) in MeOH (2mL) was left to stir at room temperature for 3 days. MeOH was removed in vacuo and DCM (5OmL) and water (5OmL) were added to the residue. The organic layer was separated and the aqueous extracted with DCM (3 x 2OmL) The combined organic layers were dried over Na2SO4, filtered and concentrated in vacuo togive 3-amino-N-methyl-benzamide (l7Omg, 1.l3mmol, 93percent yield) as a yellow oil which was used in the next step without further purification.1H NMR (CDCI3, 400MHZ) O/ppm: 7.20 (1H, t, J= 7.8Hz), 7.15 (1H, t, J= 2.0Hz), 7.05 (1H, ddd, J=7.6Hz, 1.6Hz, 1.0Hz), 6.80 (1H, dd, J= 8.0Hz, 2.4Hz), 6.14 (1H, brs), 3.70 (2H, brs), 3.01 (3H, d, J= 4.9Hz).MS Method 2: RT: 0.36 mi mlz 151.0 [M+H]

Molecular Weight:150.18
XLogP3:-0.1
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:1
Exact Mass:150.079312947
Monoisotopic Mass:150.079312947
Topological Polar Surface Area:55.1
Heavy Atom Count:11
Complexity:147
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes