Water → 2-Amino-alpha-methylbenzenemethanol

HRID 1619460Notes

Reaction equation

HRID 1619460 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[NH2:10])(=[O:3])[CH3:2].[BH4-].[Na+].O>CO>[NH2:10][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[CH:1]([OH:3])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 110862'-AminoacetophenoneHCID 4311764Sodium borohydride2×

Product 1

HCID 1120582-Amino-alpha-methylbenzenemethanolYield 80.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

That is, 1-acetyl-aminobenzene (300 mg, 2.2 mmol) was dissolved in methanol, sodium borohydride (418 mg, 11 mmol) was added, the temperature was raised from under ice-cooling to room temperature, and the mixture was stirred for 1 hr. Then, water was added to the reaction mixture, and unreacted sodium borohydride was decomposed. Then, the solvent was evaporated under reduced pressure, and the obtained residue was purified by silica gel chromatography (eluent; chloroform:methanol (30:1)) to give 1-(aminophenyl)ethanol (yield; 242 mg, 80%). According to the final step in Example 2 (step for condensing Y222 and Y491), compound Y491 (the aforementioned) (196 mg, 4.3 mmol) and 1-(aminophenyl)ethanol (147 mg, 10.8 mmol) were condensed to give the title compound (yield; 157 mg, 66%).

Workup

  1. temperaturethe temperature was raised from under ice-
  2. customThen, the solvent was evaporated under reduced pressure
  3. customthe obtained residue was purified by silica gel chromatography (eluent; chloroform:methanol (30:1))

Sources & evidence

ORD record
ord-44d2a39170154ccbb61534b9479196ab
Source dataset
uspto-grants-2014_07
Patent number
US08772297B2

Reaction notes

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