Sodium borohydride → Methyl 4-(acetylamino)-3-(hydroxymethyl)benzoate

HRID 1451078Notes

Reaction equation

HRID 1451078 reaction equation
[CH3:1][O:2][C:3](=[O:16])[C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11](=[O:13])[CH3:12])=[C:6]([CH:14]=[O:15])[CH:5]=1.[BH4-].[Na+]>CO>[CH3:1][O:2][C:3](=[O:16])[C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11](=[O:13])[CH3:12])=[C:6]([CH2:14][OH:15])[CH:5]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 12464019HCID 12464019, compound

Product 1

HCID 10609124Methyl 4-(acetylamino)-3-(hydroxymethyl)benzoateYield 99%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

Methyl-4-acetylamino-3-formylbenzoate (Gassman, P. G.; Drews, H. R. J. Am. Chem. Soc. 1978, 100, 7600-7610) (0.331 g, 0.0015 mol) was dissolved in methanol (5 mL) and cooled to 0° C. Sodium borohydride (0.057 g, 0.0015 mol) was added to the above solution at 0° C. and stirred for 0.25 h. The reaction was complete by TLC during this time. It was neutralized with H+ resin, filtered, and the filtrate concentrated. The residue was dried under vacuum over phosphorus pentoxide at 56° C. to give 0.33 g (99%) of methyl-4-acetylamino-3-hydroxymethylbenzoate as a pink solid, mp 60° C.

Workup

  1. filtrationfiltered
  2. concentrationthe filtrate concentrated
  3. dry with materialThe residue was dried under vacuum over phosphorus pentoxide at 56° C.

Sources & evidence

ORD record
ord-44c6190ce19042be9ad276c79bab8c09
Source dataset
uspto-grants-1997_02
Patent number
US05602277

Reaction notes

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