Ammonium Chloride → 2-fluoro-4-(hydroxymethyl)-N-methylbenzamide

HRID 629426Notes

Reaction equation

HRID 629426 reaction equation
[F:1][C:2]1[CH:11]=[C:10]([CH:12]=[O:13])[CH:9]=[CH:8][C:3]=1[C:4]([NH:6][CH3:7])=[O:5].[BH4-].[Na+].[Cl-].[NH4+]>CO>[F:1][C:2]1[CH:11]=[C:10]([CH2:12][OH:13])[CH:9]=[CH:8][C:3]=1[C:4]([NH:6][CH3:7])=[O:5]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 900236522-fluoro-4-formyl-N-methylbenzamide

Product 1

HCID 1179770652-fluoro-4-(hydroxymethyl)-N-methylbenzamideYield 70.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2-fluoro-4-formyl-N-methylbenzamide (0.62 g) in methanol (17 mL) was added sodium borohydride (0.16 g) in small portions, and the mixture was stirred at room temperature for 3 days. To the reaction mixture was added aqueous ammonium chloride, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (0.44 g).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-e09a5fb82f074b23b0af9ca0bc046b54
Source dataset
uspto-grants-2016_04
Patent number
US09315458B2

Reaction notes

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