Water → 1-N-methyl-4-nitrobenzene-1,2-diamine

HRID 1391524Notes

Reaction equation

HRID 1391524 reaction equation
F[C:2]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][C:3]=1[NH2:4].C(=O)([O-])[O-].[K+].[K+].[CH3:18][NH2:19].O>CN1CCCC1=O>[CH3:18][NH:19][C:2]1[C:3]([NH2:4])=[CH:5][C:6]([N+:9]([O-:11])=[O:10])=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6329MethylamineHCID 11430Potassium CarbonateHCID 677852-Fluoro-5-nitroaniline

Product 1

HCID 34200251-N-methyl-4-nitrobenzene-1,2-diamine

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

To a solution of 2-fluoro-5-nitroaniline (5 g, 32 mmol) in 40 ml N-methylpyrrolidinone in a sealed reaction vessel was added potassium carbonate (9.0 g, 50.0 mmol) and a solution of methyl amine (32 ml, 2M in THF) and the reaction was heated to 120° C. After 16 h, the reaction mixture was cooled to room temperature and poured into 400 ml of water. The resulting precipitate was filtered and dried to give the title compound as a red solid. 1H NMR (300 MHz, d6-DMSO) δ7.54 (dd, J=8.7 and 2.7 Hz, 1H), 7.39 (d, J=2.7 Hz, 1H), 6.41 (d, J=8.7 Hz, 1H), 6.13 (s, 1H), 5.08 (s, 2H), 2.83 (s, 3H).

Workup

  1. filtrationThe resulting precipitate was filtered
  2. customdried

Sources & evidence

ORD record
ord-96f3b297df2645cca9b4d870ca984e30
Source dataset
uspto-grants-2008_03
Patent number
US07338959B2

Reaction notes

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