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

HRID 1430400Notes

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+].C1(C)C=CC=CC=1.F[C:23]1[CH:24]=[CH:25][C:26]([N+:31]([O-:33])=[O:32])=[C:27]([CH:30]=1)[NH:28][CH3:29]>[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[CH2:1]([O:8][C:23]1[CH:24]=[CH:25][C:26]([N+:31]([O-:33])=[O:32])=[C:27]([CH:30]=1)[NH:28][CH3:29])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 65 °C

Procedure

Benzyl alcohol (49.6 mL, 0.48 mol), tetrabutyl ammonium chloride (6.66 g, 24.0 mmol) and potassium carbonate (40.0 g, 0.29 mol) were added to a toluene solution (200 mL) of 5-fluoro-N-methyl-2-nitroaniline (40.8 g, 0.24 mol), and the mixture was heated under reflux for 3.5 hours. The reaction solution was cooled, and 100 mL of water was added thereto. Thereafter, the mixture was stirred for 1 hour at 60 to 70° C. After the mixture was stirred under ice cooling for 30 minutes, precipitated crystals were collected by filtration. The resulting crystals were washed with water, and dried at 50° C., thereby obtaining 57.1 g of an orange, powdery target compound (yield: 92%).

Workup

temperaturethe mixture was heated
temperatureunder reflux for 3.5 hours
temperatureThe reaction solution was cooled
stirringAfter the mixture was stirred under ice cooling for 30 minutes
customprecipitated crystals
filtrationwere collected by filtration
washThe resulting crystals were washed with water
customdried at 50° C.

Sources & evidence

ORD record: ord-5b196df8704a4b269a2393375eb08724
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08940889B2

Reaction notes

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