Methylamine → Phenol, 3-(methylamino)-4-nitro-

HRID 1777121Notes

Reaction equation

HRID 1777121 reaction equation
F[C:2]1[CH:3]=[C:4]([OH:11])[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9].[CH3:12][NH2:13]>O.Cl>[CH3:12][NH:13][C:2]1[CH:3]=[C:4]([OH:11])[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9]

Participants

5

Reactant 2

HCID 6329MethylamineHCID 5209483-Fluoro-4-nitrophenol

Product 1

HCID 146175Phenol, 3-(methylamino)-4-nitro-Yield 95%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Procedure

The solution of 3-fluoro-4-nitrophenol (1 g, 6.37 mmol) in aqueous MeNH2 solution (5 mL) was stirred at 85° C. for 5 h. After cooling to room temperature, the solution was diluted with water (30 mL) and concentrated HCl added to adjust to pH 1. The resulting precipitate was collected by filtration and the solid dried under vacuum to give the crude product which was used without further purification (1.1 g, 95% yield). LCMS (m/z): 169.1 (M+1).

Workup

  1. additionadded
  2. filtrationThe resulting precipitate was collected by filtration
  3. customthe solid dried under vacuum

Sources & evidence

ORD record
ord-48d19bdcfb3b43c7b40fb873ccdeffb8
Source dataset
uspto-grants-2016_02
Patent number
US09266836B2

Reaction notes

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