N,N-dimethyl-4-nitro-2-(trifluoromethyl)benzamide → 4-Amino-N,N-dimethyl-2-trifluoromethylbenzamide

HRID 576222Notes

Reaction equation

[CH3:1][N:2]([CH3:18])[C:3](=[O:17])[C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-])=O)=[CH:6][C:5]=1[C:13]([F:16])([F:15])[F:14]>CO.[Pd]>[NH2:10][C:7]1[CH:8]=[CH:9][C:4]([C:3]([N:2]([CH3:1])[CH3:18])=[O:17])=[C:5]([C:13]([F:14])([F:15])[F:16])[CH:6]=1

Participants

Conditions

Temperature: 20 °C

Procedure

To a solution of N,N-dimethyl-4-nitro-2-(trifluoromethyl)benzamide (10 g, 25.2 mmol) in MeOH (100 mL) stirred under N2 at 20° C. was added Pd/C (1 g, 9.40 mmol) in one charge. The reaction mixture stirred under a H2 atmosphere at 20° C. for 12 h. The mixture was filtered, and the filtrate was concentrated in vacuo to give the desired product 4-amino-N,N-dimethyl-2-(trifluoromethyl)benzamide (8.3 g, 23.59 mmol, 94.0% yield). TLC (DCM/MeOH=10:1, Rf=0.4): 1H NMR (400 MHz, CDCl3) δ 7.07 (d, J=8.2 Hz, 1H), 6.90 (s, 1H), 6.79 (d, J=8.2 Hz, 1H), 3.95 (br. s., 2H), 3.08 (s, 3H), 2.80 (s, 3H); ES-LCMS m/z 233.0 (M+H).

Workup

additioncharge
filtrationThe mixture was filtered
concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record: ord-0c3f1939080e4c1080326b40db2dad77
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09035063B2

Reaction notes

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