Methyl 2-amino-5-bromobenzoate → 2-Amino-5-bromo-N-methylbenzamide

HRID 511291Notes

Reaction equation

[NH2:1][C:2]1[CH:11]=[CH:10][C:9]([Br:12])=[CH:8][C:3]=1[C:4](OC)=[O:5].[CH3:13][NH2:14].O>O>[NH2:1][C:2]1[CH:11]=[CH:10][C:9]([Br:12])=[CH:8][C:3]=1[C:4]([NH:14][CH3:13])=[O:5]

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of methyl 2-amino-5-bromobenzoate (Compound 106B, 65 g) and CH3NH2.H2O (1000 mL) was stirred at 80° C. overnight in a pressure tube. The mixture was diluted with H2O (1000 mL) and extracted with EtOAc (3×500 mL). The combined organic layers were dried over MgSO4, concentrated to afford the title compound (55 g, yield: 87%) as a gray solid. 1H NMR (CDCl3, 400 MHz): δ=2.93 (d, J=5.2 Hz, 3 H), 5.48 (s, br, 2 H), 6.04 (s, br, 1 H), 6.54 (d, J=8.4 Hz, 1 H), 7.24 (dd, J=2.0, 8.4 Hz, 1 H), 7.38 (d, J=2.0 Hz, 1 H).

Workup

extractionextracted with EtOAc (3×500 mL)
dry with materialThe combined organic layers were dried over MgSO4
concentrationconcentrated

Sources & evidence

ORD record: ord-13c65305239f46ab8b8d2ae164d16746
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09096624B2

Reaction notes

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