Ammonium Chloride → 4-[Hydroxy(4-methoxyphenyl)methyl]benzonitrile

HRID 363049Notes

Reaction equation

HRID 363049 reaction equation
[CH3:1][O:2][C:3]1[CH:18]=[CH:17][C:6]([C:7]([C:9]2[CH:16]=[CH:15][C:12]([C:13]#[N:14])=[CH:11][CH:10]=2)=[O:8])=[CH:5][CH:4]=1.[BH4-].[Na+].[Cl-].[NH4+]>C(O)C>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH:7]([OH:8])[C:9]2[CH:10]=[CH:11][C:12]([C:13]#[N:14])=[CH:15][CH:16]=2)=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 108683214-(4-Methoxybenzoyl)benzonitrile

Product 1

HCID 112419044-[Hydroxy(4-methoxyphenyl)methyl]benzonitrile

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of 4-(4-methoxybenzoyl)benzonitrile 26-1 (J. Med. Chem. 1991, 34, 2768-2778) (0.783 g, 3.3 mmol) in ethanol (35 ml) under nitrogen cooled in an ice-bath was added sodium borohydride (0.250 g, 6.6 mmol). The mixture was stirred 4 h with ice-bath cooling. To the resulting solution was added saturated ammonium chloride solution (35 ml). The mixture was partially evaporated under reduced pressure, and the resulting aqueous mixture was extracted with ethyl acetate (2×100 ml). The combined organic fractions were washed with brine (50 ml), dried (sodium sulfate), and the solvent was evaporated under reduced pressure. The residue was purified by flash column chromatography on silica gel, eluting with ethyl acetate/hexane (1:6 increasing to 1:3), to give product 26-2 as an oil.

Workup

  1. temperaturecooled in an ice-bath
  2. temperaturecooling
  3. customThe mixture was partially evaporated under reduced pressure
  4. extractionthe resulting aqueous mixture was extracted with ethyl acetate (2×100 ml)
  5. washThe combined organic fractions were washed with brine (50 ml)
  6. dry with materialdried (sodium sulfate)
  7. customthe solvent was evaporated under reduced pressure
  8. customThe residue was purified by flash column chromatography on silica gel
  9. washeluting with ethyl acetate/hexane (1:6 increasing to 1:3)

Sources & evidence

ORD record
ord-6e1d016534724a41bb7df789afa80dfd
Source dataset
uspto-grants-1999_02
Patent number
US05872138

Reaction notes

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