O-Toluidine → N-Benzyl-o-toluidine

HRID 323134

Reaction equation

HRID 323134 reaction equation
[CH3:1][C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[NH2:4].C(N(CC)CC)C.[CH2:16](Br)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>CN(C)C=O.C(OCC)(=O)C>[CH2:16]([NH:4][C:3]1[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=1[CH3:1])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 3

HCID 7242O-ToluidineHCID 7498Benzyl BromideHCID 8471Triethylamine

Product 1

HCID 79402N-Benzyl-o-toluidineYield 43.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-methylaniline (1.0 g) and triethylamine (0.95 g) in N,N-dimethylformamide (15 ml) was added benzyl bromide (1.9 g) at ambient temperature and the mixture was stirred at ambient temperature overnight. The reaction mixture was diluted with ethyl acetate and it was washed with water and brine. Drying, filtering and the removal of solvents afforded a crude product. The crude product was chromatographed on silica gel (n-hexane:ethyl acetate=10:1) to give N-benzyl-2-methylaniline (795 mg) as a slightly yellow oil.

Workup

  1. washwas washed with water and brine
  2. customDrying
  3. filtrationfiltering
  4. customthe removal of solvents
  5. customafforded a crude product
  6. customThe crude product was chromatographed on silica gel (n-hexane:ethyl acetate=10:1)

Sources & evidence

ORD record
ord-05f846309ebb430c9ce70a7852c1dbbf
Source dataset
uspto-grants-2001_04
Patent number
US06211242B1

Linked notes

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