Methanol → HCID 20026626, compound

HRID 1723115Notes

Reaction equation

HRID 1723115 reaction equation
[CH3:1][NH:2][C:3]1[CH:8]=[CH:7][C:6]([C:9](=[O:11])[CH3:10])=[CH:5][C:4]=1[N+:12]([O-:14])=[O:13].CO.[BH4-].[Na+]>O>[CH3:10][CH:9]([C:6]1[CH:7]=[CH:8][C:3]([NH:2][CH3:1])=[C:4]([N+:12]([O-:14])=[O:13])[CH:5]=1)[OH:11]

Participants

5

Reactant 3

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 131756261-[4-(Methylamino)-3-nitrophenyl]ethan-1-one

Product 1

HCID 20026626HCID 20026626, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

(a-2) To a stirred mixture of 19.4 parts of 1-[4-(methylamino)-3-nitrophenyl]ethanone and 160 parts of methanol were added dropwise 4 parts of sodium tetrahydroborate. Upon complete addition, stirring was continued for 1 hour at room temperature. The reaction mixture was poured into 1000 parts of water and the product was extracted three times with 120 parts of trichloromethane. The combined extracts were dried, filtered and evaporated. The residue was purified by column chromatography over silica gel using a mixture of trichloromethane and methanol (98:2 by volume) as eluent. The pure fractions were collected and the eluent was evaporated, yielding 17 parts (89%) of α-methyl-4-(methylamino)-3-nitrobenzenemethanol as a residue (int. 88).

Workup

  1. additionUpon complete addition
  2. extractionthe product was extracted three times with 120 parts of trichloromethane
  3. customThe combined extracts were dried
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by column chromatography over silica gel using
  7. additiona mixture of trichloromethane and methanol (98:2 by volume) as eluent
  8. customThe pure fractions were collected
  9. customthe eluent was evaporated

Sources & evidence

ORD record
ord-58c1ae7de4e24f07acabe99e702a4b1c
Source dataset
uspto-grants-1989_08
Patent number
US04859684

Reaction notes

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