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

HRID 649306Notes

Reaction equation

HRID 649306 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-phenylhexanamide (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. Then, unreacted N,N-dimethylhydrazine and the resulted water, together with about 2 ml of toluene were distilled off outside the reaction system. 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 was dropwise added to the remaining solution over a period of 30 minutes, while refluxing. The mixture was further refluxed for 2.5 hours and 3 ml of toluene was distilled off outside the reaction system. The reaction mixture was cooled to room temperature. The resulted crystals were filtered off, washed and dried to obtain 1.32 g (Yield: 49%) of the title compound.

Workup

  1. distillationThen, unreacted N,N-dimethylhydrazine and the resulted water, together with about 2 ml of toluene were distilled off outside the reaction system
  2. additionA 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 was dropwise added to the remaining solution over a period of 30 minutes
  3. temperaturewhile refluxing
  4. temperatureThe mixture was further refluxed for 2.5 hours
  5. distillation3 ml of toluene was distilled off outside the reaction system
  6. temperatureThe reaction mixture was cooled to room temperature
  7. filtrationThe resulted crystals were filtered off
  8. washwashed
  9. customdried

Sources & evidence

ORD record
ord-e69b6b799f154b3c8c2ea2d0f0436dc9
Source dataset
uspto-grants-1988_04
Patent number
US04739083

Reaction notes

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