1,1-Dimethylhydrazine → 6-Methyl-4-oxo-N-phenyl-2-propyl-4H-pyran-3-carboxamide

HRID 476818Notes

Reaction equation

HRID 476818 reaction equation
[O:1]=[C:2]([CH2:13][CH2:14][CH3:15])[CH2:3][C:4]([NH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:5].CN(C)N>C1(C)C=CC=CC=1>[CH3:15][C:14]1[O:1][C:2]([CH2:13][CH2:14][CH3:15])=[C:3]([C:4]([NH:6][C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[O:5])[C:2](=[O:1])[CH:13]=1

Participants

4

Reactant 2

HCID 59761,1-DimethylhydrazineHCID 3384353-oxo-N-phenylhexanamide

Product 1

HCID 138540146-Methyl-4-oxo-N-phenyl-2-propyl-4H-pyran-3-carboxamideYield 97.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 2.05 g (10 m mol) of 3-oxo-N-phenyl hexanamide (m.p. 77.0°~78.5° C.), 0.9 g (15 m mol) of N,N-dimethylhydrazine and 15 ml of toluene was stirred for 8 hours at 60° C. and further heated to a more elevated temperature to distill off the unreacted N,N-dimethylhydrazine and the resulted water together with about 2 ml of toluene. While refluxing, to the mixture was dropwise added a solution of 3.90 g (25 m mol) of 2-ethyl-2,6-dimethyl-4H-1,3-dioxin-4-one in 8 ml of toluene during 30 minutes. While refluxing for 2.5 hours, 3 ml of toluene was removed. After cooling to room temperature, the precipitated crystals were separated, washed and dried under vacuo to afford 1.32 g of the title compound (yield: 49%).

Workup

  1. temperaturefurther heated to a more elevated temperature
  2. distillationto distill off the unreacted N,N-dimethylhydrazine
  3. temperatureWhile refluxing, to the mixture
  4. additionwas dropwise added a solution of 3.90 g (25 m mol) of 2-ethyl-2,6-dimethyl-4H-1,3-dioxin-4-one in 8 ml of toluene during 30 minutes
  5. temperatureWhile refluxing for 2.5 hours
  6. custom3 ml of toluene was removed
  7. temperatureAfter cooling to room temperature
  8. customthe precipitated crystals were separated
  9. washwashed
  10. customdried under vacuo

Sources & evidence

ORD record
ord-3657d92a76574520bb7efb92d6503278
Source dataset
uspto-grants-1989_12
Patent number
US04886546

Reaction notes

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