Dimethylformamide dimethyl acetal → HCID 59006708, compound

HRID 2243895Notes

Reaction equation

HRID 2243895 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[C:9]([CH3:11])[NH:8][C:7](=[O:12])[CH:6]=1)=[O:4].[CH3:13]OC(OC)N(C)C>CN(C=O)C>[CH3:1][O:2][C:3]([C:5]1[CH:10]=[C:9]([CH3:11])[N:8]([CH3:13])[C:7](=[O:12])[CH:6]=1)=[O:4]

Participants

4

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 14117784Methyl 6-methyl-2-oxo-1,2-dihydropyridine-4-carboxylate

Product 1

HCID 59006708HCID 59006708, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A suspension of the title compound of Example 33.1 (0.80 g, 4.8 mmol) and dimethylformamide dimethylacetal (3.2 mL, 24 mmol) in DMF (10 mL) was heated at 60° C. for 48 hours. The reaction mixture was concentrated and the residue was dissolved in dichloromethane and washed with water. The organic layer was concentrated. Recrystallization from ethyl acetate/heptane afforded the title compound (423 mg, 49%)

Workup

  1. concentrationThe reaction mixture was concentrated
  2. dissolutionthe residue was dissolved in dichloromethane
  3. washwashed with water
  4. concentrationThe organic layer was concentrated
  5. customRecrystallization from ethyl acetate/heptane

Sources & evidence

ORD record
ord-51d03a101718429a991bcceffa9515e9
Source dataset
uspto-grants-2010_03
Patent number
US07678796B2

Reaction notes

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