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

HRID 1430401Notes

Reaction equation

HRID 1430401 reaction equation
[CH2:1]([OH:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O.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>[CH2:1]([O:8][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:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 244Benzyl AlcoholHCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 229057745-fluoro-N-methyl-2-nitroaniline

Product 1

HCID 679540515-benzyloxy-N-methyl-2-nitroanilineYield 88%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
65 °C

Procedure

Benzyl alcohol (0.93 mL, 9 mmol) and potassium carbonate (1.24 g, 9 mmol) were added to a N,N-dimethyl formamide solution (5 mL) of 5-fluoro-N-methyl-2-nitroaniline (510 mg, 3 mmol). The mixture was stirred at 60-70° C. for 8 hours. The reaction solution was cooled, then water was added thereto, and precipitated crystals were collected by filtration. The resulting crystals were washed with water, and dried at 50° C., thereby obtaining 680 mg of orange, powdery 5-benzyloxy-N-methyl-2-nitroaniline (yield: 88%).

Workup

  1. temperatureThe reaction solution was cooled
  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-0f1bfc3c5c1b41d48a72f9c7ec264e75
Source dataset
uspto-grants-2015_01
Patent number
US08940889B2

Reaction notes

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