Dimethylformamide dimethyl acetal → N-formyl-2-(o-methylphenyl)acetamide

HRID 2232970Notes

Reaction equation

HRID 2232970 reaction equation
[C:1]1([CH3:11])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][C:8]([NH2:10])=[O:9].[CH3:12][O:13]C(OC)N(C)C>C(O)(=O)C>[CH:12]([NH:10][C:8](=[O:9])[CH2:7][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=1[CH3:11])=[O:13]

Participants

4

Reactant 2

HCID 78373Dimethylformamide dimethyl acetal2×HCID 171457242-(2-Methylphenyl)acetamide

Product 1

HCID 86612382N-formyl-2-(o-methylphenyl)acetamide

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 2-o-tolylacetamide (Lee, Dong-Ung; Mayer, Klaus K.; Wiegrebe, Wolfgang; Lauber, Rolf; Schlunegger, Urs P.; Arch. Pharm. 1988, 321; 265-272) (320 mg, 2.15 mmol) and N,N,-dimethylformamide dimethylacetal (1.1 mL, 8.59 mmol) was stirred under N2 for 55 min at 120° C. The excess of N,N,-dimethylformamide dimethylacetal was eliminated under reduced pressure. The residue was dissolved in 3 mL of 70% aqueous acetic acid and stirred at 0° C. for 30 min. The precipitate was filtered, washed with water and dried to afford the title compound as a white solid. MS (DCI/NH3) m/z 195 (M+NH4)+.

Workup

  1. stirringstirred at 0° C. for 30 min
  2. filtrationThe precipitate was filtered
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-4eb2ef6e4b1c46359dbbf5d84023a2e4
Source dataset
uspto-grants-2010_05
Patent number
US07709469B2

Reaction notes

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