Hydrochloric Acid → HCID 18423003, compound

HRID 1282056Notes

Reaction equation

HRID 1282056 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][NH:11][C:12](=[O:14])[CH3:13])=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[BH4-].[Na+].Cl>CO>[OH:3][CH:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][NH:11][C:12](=[O:14])[CH3:13])=[CH:6][CH:5]=1)[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 18423154HCID 18423154, compound

Product 1

HCID 18423003HCID 18423003, compoundYield 102.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
6 °C

Procedure

To a solution of N-[(4-acetylphenyl)methyl]acetamide (6.1 g) in methanol (50 ml) was added sodium borohydride (1.2 g) under ice-cooling. This reaction mixture was stirred at 5-7° C. for 2 hr. Thereto was added 2% hydrochloric acid and extracted with ethyl acetate (100 ml×3). The ethyl acetate layer was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated to give a brown oil (6.3 g). The obtained brown oil was purified by silica gel column chromatography (developing solvent; chloroform:methanol=9:1) to give the title compound (5.98 g) as a pale-brown oil, m.p.=61-62° C.

Workup

  1. temperaturecooling
  2. extractionextracted with ethyl acetate (100 ml×3)
  3. washThe ethyl acetate layer was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was evaporated

Sources & evidence

ORD record
ord-f198bd4927fa460e9519c8c401316f7c
Source dataset
uspto-grants-2002_09
Patent number
US06455528B1

Reaction notes

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