Water → Benzenamine, 5-methoxy-N-methyl-2-nitro-

HRID 33391

Reaction equation

HRID 33391 reaction equation
[CH3:1][NH2:2].F[C:4]1[CH:5]=[C:6]([O:13][CH3:14])[CH:7]=[CH:8][C:9]=1[N+:10]([O-:12])=[O:11].C(=O)([O-])[O-].[K+].[K+].O>C1COCC1.ClCCl>[CH3:14][O:13][C:6]1[CH:7]=[CH:8][C:9]([N+:10]([O-:12])=[O:11])=[C:4]([NH:2][CH3:1])[CH:5]=1

Participants

7

Reactant 4

HCID 962WaterHCID 6329MethylamineHCID 11430Potassium CarbonateHCID 5656543-Fluoro-4-nitroanisole

Product 1

HCID 153056Benzenamine, 5-methoxy-N-methyl-2-nitro-

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

83.5 mL (167.0 mmol) of a 2 molar solution of methylamine in THF are added dropwise to 14.3 g (83.56 mmol) 3-fluoro-4-nitro-anisol and 12.71 g (92.02 mmol) potassium carbonate in 200 mL dichloromethane. The mixture is stirred overnight and then combined with water. The organic phase is washed successively with water and ammonium chloride solution, dried and evaporated down. The yellow solid remaining is stirred with hexane. Yield: 12.7 g (84%); mass spectroscopy: [M+H]+=183.

Workup

  1. washThe organic phase is washed successively with water and ammonium chloride solution
  2. customdried
  3. customevaporated down
  4. stirringThe yellow solid remaining is stirred with hexane

Sources & evidence

ORD record
ord-bc918e6a5f98444a864a487a48b4fb21
Source dataset
uspto-grants-2008_09
Patent number
US07429583B2

Linked notes

Loading…