Methylamine → Benzenamine, N-methyl-2-nitro-4-(trifluoromethyl)-

HRID 1494333Notes

Reaction equation

HRID 1494333 reaction equation
[CH3:1][NH2:2].F[C:4]1[CH:9]=[CH:8][C:7]([C:10]([F:13])([F:12])[F:11])=[CH:6][C:5]=1[N+:14]([O-:16])=[O:15]>CN(C)C=O>[CH3:1][NH:2][C:4]1[CH:9]=[CH:8][C:7]([C:10]([F:13])([F:12])[F:11])=[CH:6][C:5]=1[N+:14]([O-:16])=[O:15]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 677784-Fluoro-3-nitrobenzotrifluoride

Product 1

HCID 88405Benzenamine, N-methyl-2-nitro-4-(trifluoromethyl)-Yield 86%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A stream of methylamine was bubbled through a solution of 1.3 g (6.2 mmol) 4-fluoro-3-nitrobenzotrifluoride in 25 ml dimethylformamide at 25° C. for 5 min. Stirring was continued at 25° C. for 2 h, and then the reaction mixture was evaporated in vacuo. The residue was stirred with water, and the precipitate was filtered off to give 1.17 g (86%) 4-methylamino-3-nitrobenzotrifluoride. NMR (CDCl3): 8.4 (1H, s), 8.2 (1H, broad s), 7.6 (1H, dd), 6.9 (1H, d), 3.1 (3H, d).

Workup

  1. customthe reaction mixture was evaporated in vacuo
  2. stirringThe residue was stirred with water
  3. filtrationthe precipitate was filtered off

Sources & evidence

ORD record
ord-9966705f7d0d41cbabbf9ac7e647fa3d
Source dataset
uspto-grants-1991_06
Patent number
US05026704

Reaction notes

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