Dimethylformamide → N-(3-formylphenyl)acetamide

HRID 2102366Notes

Reaction equation

HRID 2102366 reaction equation
[OH:1][CH2:2][C:3]1[CH:4]=[C:5]([NH:9][C:10](=[O:12])[CH3:11])[CH:6]=[CH:7][CH:8]=1.[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.CN(C)C=O>ClCCl>[CH:2]([C:3]1[CH:4]=[C:5]([NH:9][C:10](=[O:12])[CH3:11])[CH:6]=[CH:7][CH:8]=1)=[O:1]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 966393-Acetaminobenzyl alcoholHCID 178418287HCID 178418287, compound

Product 1

HCID 256849N-(3-formylphenyl)acetamideYield 81%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of N-(3-hydroxymethylphenyl)acetamide (165 mg, 1.0 mmol), celite (165 mg), pyridinium chlorochromate (645 mg, 3.0 mmol), N,N-dimethylformamide (1.0 mL) and dichloromethane (25 mL) was stirred at room temperature for 24 h. The reaction mixture was filtered and concentrated in vacuo. The resulting residue was dissolved in dichloromethane (40 mL) and washed with aqueous sodium bicarbonate solution (2×30 mL). The organic layer was concentrated and the product purified by chromatography over silica gel using ethyl acetate/hexanes (1:1) as eluant to give 130 mg (81%) of N-(3-formylphenyl)acetamide as a brown solid. MS [M+H] 164.2, 1H NMR (CDCl3) δ (ppm) 9.96 (s, 1H), 8.22 (b, 1H), 8.03 (s, 1H), 7.89 (d, J=7.8 Hz, 1H), 7.61 (d, J=6.6 Hz, 1H), 7.47 (t, J=7.8 Hz, 1H), 2.22 (s, 1H).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated in vacuo
  3. dissolutionThe resulting residue was dissolved in dichloromethane (40 mL)
  4. washwashed with aqueous sodium bicarbonate solution (2×30 mL)
  5. concentrationThe organic layer was concentrated
  6. customthe product purified by chromatography over silica gel

Sources & evidence

ORD record
ord-fd47da2c953a43578f80c56371273eb7
Source dataset
uspto-grants-2009_08
Patent number
US07576080B2

Reaction notes

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