Water → N-Methyl-4-benzyloxy-2-methylaniline

HRID 1010404Notes

Reaction equation

HRID 1010404 reaction equation
[CH2:1]([O:8][C:9]1[CH:15]=[CH:14][C:12]([NH2:13])=[C:11]([CH3:16])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1(CO)C2C=CC=C[C:20]=2N=N1.[BH4-].[Na+].O>CN(C)C=O.CO.C(OCC)(=O)C>[CH3:20][NH:13][C:12]1[CH:14]=[CH:15][C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[CH:10][C:11]=1[CH3:16]

Participants

8

Reactant 4

HCID 962WaterHCID 2241691H-Benzotriazole-1-methanolHCID 4311764Sodium borohydrideHCID 167730534-(Benzyloxy)-2-methylaniline

Product 1

HCID 22936498N-Methyl-4-benzyloxy-2-methylanilineYield 62.5%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

After dissolving 4-benzyloxy-2-methylaniline (6.55 g, 30.72 mmol) in N,N-dimethylformamide (10 ml) and methanol (60 ml), 1H-benzotriazole-1-methanol (4.58 g, 30.72 mmol) was added and the mixture was stirred for 30 minutes at room temperature. N,N-Dimethylformamide (20 ml) was added for complete dissolution of the precipitated crystals, sodium borohydride (2.32 g, 61.44 mmol) was added in small portions at a time at room temperature (internal temperature increase), and the mixture was stirred for 30 minutes. Water was added to the reaction solution, extraction was performed ethyl acetate, the extract was washed with saturated brine and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was adsorbed onto silica gel and purified by silica gel column chromatography (hexane-ethyl acetate) to obtain the title compound (4.364 g, 19.20 mmol, 62.49%) as a brown oil.

Workup

  1. additionwas added
  2. additionwas added in small portions at a time at room temperature
  3. temperature(internal temperature increase)
  4. stirringthe mixture was stirred for 30 minutes
  5. washthe extract was washed with saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationthe solvent was distilled off under reduced pressure
  8. custompurified by silica gel column chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-91f8bdb10a654ebebb34ac3d7bd5ee70
Source dataset
uspto-grants-2011_07
Patent number
US07973160B2

Reaction notes

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