Acetic Anhydride → N-formyl-N-benzyloxyamine

HRID 581104Notes

Reaction equation

HRID 581104 reaction equation
[CH2:1]([O:8][NH2:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:10](OC(=O)C)(=[O:12])C>C(O)=O>[CH2:1]([O:8][NH:9][CH:10]=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 7918Acetic Anhydride2×HCID 102313O-Benzylhydroxylamine

Product 1

HCID 11423690N-formyl-N-benzyloxyamineYield 60%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

O-benzylhydroxylamine (4.63 g, 37 mmol) was dissolved into 89% formic acid (80 ml), and 30 ml of acetic anhydride was added dropwise thereto with keeping the temperature at 50 to 60° C. After adding acetic anhydride, the solution was stirred for 2 hours at room temperature. The organic layer was rinsed and dried, and the solvent was evaporated. The residue was then purified with silica gel chromatography to obtain 3.05 g of N-benzyloxyformamide (yield: 60%). The proton NMR spectrum of the compound is 4.82 bs, 4.93 bs (2H); 7.20-7.47 m (5H); 7.93 bs, 8.30 bs (1H) (solvent: CDCl3).

Workup

  1. additionwas added dropwise
  2. customat 50 to 60° C
  3. washThe organic layer was rinsed
  4. customdried
  5. customthe solvent was evaporated
  6. customThe residue was then purified with silica gel chromatography

Sources & evidence

ORD record
ord-ff3d102ecad1414f8f96a3a6718aed52
Source dataset
uspto-grants-1999_07
Patent number
US05919825

Reaction notes

Loading…