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

HRID 1391542Notes

Reaction equation

HRID 1391542 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 (3.0 g, 19.2 mmol) in 24 ml N-methylpyrrolidinone in a sealed reaction vessel was added potassium carbonate (5.4 g, 30.0 mmol) and a solution of methyl amine (20 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 200 ml of water. The resulting precipitate was filtered and dried to give the title compound as a red solid. MS (ESI) m/z=168 [M+H].

Workup

  1. filtrationThe resulting precipitate was filtered
  2. customdried

Sources & evidence

ORD record
ord-209e45a04f614f3bb68409a536d514c5
Source dataset
uspto-grants-2008_03
Patent number
US07338959B2

Reaction notes

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