Benzyl Alcohol → 5-benzyloxy-N-methyl-2-nitroaniline

HRID 1430402Notes

Reaction equation

HRID 1430402 reaction equation
CC(C)([O-])C.[Na+].CN(C)C=O.[CH2:12]([OH:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.F[C:21]1[CH:22]=[CH:23][C:24]([N+:29]([O-:31])=[O:30])=[C:25]([CH:28]=1)[NH:26][CH3:27]>O>[CH2:12]([O:19][C:21]1[CH:22]=[CH:23][C:24]([N+:29]([O-:31])=[O:30])=[C:25]([CH:28]=1)[NH:26][CH3:27])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 244Benzyl AlcoholHCID 6228DimethylformamideHCID 229057745-fluoro-N-methyl-2-nitroanilineHCID 23676156Sodium t-butoxide

Product 1

HCID 679540515-benzyloxy-N-methyl-2-nitroanilineYield 92%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Sodium t-butoxide (865 mg, 9 mmol) was added to a N,N-dimethylformamide (5 mL) solution of benzyl alcohol (0.93 mL, 9 mmol), and the mixture was stirred at room temperature for 30 minutes. Thereafter, 5-fluoro-N-methyl-2-nitroaniline (510 mg, 3 mmol) was added thereto, and the mixture was stirred at room temperature for 3 hours. Water was added to the reaction solution, and precipitated crystals were collected by filtration. The resulting crystals were washed with water, and dried at 50° C., thereby obtaining 710 mg of orange, powdery 5-benzyloxy-N-methyl-2-nitroaniline (yield: 92%).

Workup

  1. stirringthe mixture was stirred at room temperature for 3 hours
  2. customprecipitated crystals
  3. filtrationwere collected by filtration
  4. washThe resulting crystals were washed with water
  5. customdried at 50° C.

Sources & evidence

ORD record
ord-02d2e3da0d96452c9c238046206976ed
Source dataset
uspto-grants-2015_01
Patent number
US08940889B2

Reaction notes

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