2-Aminobenzyl alcohol → [2-(Propan-2-ylamino)phenyl]methanol

HRID 1898939Notes

Reaction equation

HRID 1898939 reaction equation
[BH4-].[Na+].[NH2:3][C:4]1[CH:11]=[CH:10][CH:9]=[CH:8][C:5]=1[CH2:6][OH:7].O.O.O.[C:15]([O-])(=O)[CH3:16].[Na+].[C:20](=O)([O-])O.[Na+]>CC(C)=O.C(O)C.O.C(O)(=O)C>[CH:15]([NH:3][C:4]1[CH:11]=[CH:10][CH:9]=[CH:8][C:5]=1[CH2:6][OH:7])([CH3:16])[CH3:20]

Participants

9

Reactant 4

HCID 214392-Aminobenzyl alcoholHCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 23665404Sodium Acetate Trihydrate

Product 1

HCID 10797123[2-(Propan-2-ylamino)phenyl]methanol

Reagents, catalysts & solvents 4

HCID 176Acetic AcidSolventHCID 180AcetoneSolventHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

While maintaining at 0° to 5° C., 10 g of sodium borohydride was added by several portions to a mixture of 10 g of 2-aminobenzyl alcohol, 13.3 g of sodium acetate trihydrate, 40 ml of acetic acid, 80 ml of water, 30 ml of ethanol and 30 ml of acetone. After stirring for an hour at the same temperature, the reaction mixture was neutralized with sodium hydrogen carbonate followed by extraction with ethyl acetate. The organic layer was washed with water and then with saturated sodium chloride aqueous solution followed by drying over anhydrous magnesium sulfate. After the solvent was distilled off in vacuo, the resulting oily substance was purified by silica gel column chromatography (hexane:ethyl acetate=2:1) and then distilled in vacuo to give 9.6 g of 2-isopropylaminobenzyl alcohol.

Workup

  1. temperatureWhile maintaining at 0° to 5° C.
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe organic layer was washed with water
  4. dry with materialby drying over anhydrous magnesium sulfate
  5. distillationAfter the solvent was distilled off in vacuo
  6. customthe resulting oily substance was purified by silica gel column chromatography (hexane:ethyl acetate=2:1)
  7. distillationdistilled in vacuo

Sources & evidence

ORD record
ord-b7314a55a9b445eb934cb6f709037186
Source dataset
uspto-grants-1996_11
Patent number
US05571820

Reaction notes

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