Hydrochloric Acid → 2-Amino-1-(2,3-dichlorophenyl)ethanol

HRID 709143Notes

Reaction equation

HRID 709143 reaction equation
Cl.[NH2:2][CH2:3][C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([Cl:12])[C:7]=1[Cl:13])=[O:5].[BH4-].[Na+].Cl>CO>[NH2:2][CH2:3][CH:4]([C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([Cl:12])[C:7]=1[Cl:13])[OH:5]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 22151845Ethanone, 2-amino-1-(2,3-dichlorophenyl)-, hydrochloride

Product 1

HCID 186281262-Amino-1-(2,3-dichlorophenyl)ethanol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Under argon, 300 mg (1.25 mmol) of the compound of Example 41A were initially charged in 2 ml of methanol. 189 mg (5.0 mmol) of sodium borohydride were added and the mixture was stirred overnight. 1 N hydrochloric acid was added slowly until the evolution of gas had ceased, and the methanol was then removed on a rotary evaporator. The aqueous residue was made alkaline by addition of sodium bicarbonate solution and extracted three times with ethyl acetate. The combined organic phases were dried over sodium sulphate and freed from the solvent on a rotary evaporator. The residue (189 mg, 74% of theory) corresponded to the title compound.

Workup

  1. customthe methanol was then removed on a rotary evaporator
  2. additionby addition of sodium bicarbonate solution
  3. extractionextracted three times with ethyl acetate
  4. dry with materialThe combined organic phases were dried over sodium sulphate
  5. customfreed from the solvent on a rotary evaporator

Sources & evidence

ORD record
ord-ff67e5a48f704ef284258adc7df297fd
Source dataset
uspto-grants-2015_11
Patent number
US09180120B2

Reaction notes

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