Dimethylformamide dimethyl acetal → Methyl 5-methoxy-4-oxo-1-phenyl-1,4-dihydropyridazine-3-carboxylate

HRID 333735Notes

Reaction equation

HRID 333735 reaction equation
[CH3:1][O:2][CH2:3][C:4](=[O:18])[C:5](=[N:10][NH:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:6]([O:8][CH3:9])=[O:7].[CH3:19]OC(OC)N(C)C>>[CH3:1][O:2][C:3]1[C:4](=[O:18])[C:5]([C:6]([O:8][CH3:9])=[O:7])=[N:10][N:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:19]=1

Participants

3

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 178496274HCID 178496274, compound

Product 1

HCID 89586545Methyl 5-methoxy-4-oxo-1-phenyl-1,4-dihydropyridazine-3-carboxylate

Conditions

Temperature
90 °C

Procedure

A suspension of methyl 4-methoxy-3-oxo-2-(phenylhydrazono)butanoate (25.03 g) in dimethylformamide dimethylacetal (120 mL) was stirred at 90° C. for 1 hr. The mixture was allowed to cool to room temperature, and stirred for 1 hr. The precipitate was collected by filtration, washed successively with diethyl ether and hexane, and dried to give the title compound (24.7 g) as pale-yellow crystals.

Workup

  1. temperatureto cool to room temperature
  2. stirringstirred for 1 hr
  3. filtrationThe precipitate was collected by filtration
  4. washwashed successively with diethyl ether and hexane
  5. customdried

Sources & evidence

ORD record
ord-1dd6ffb3bcad4d91b9b5ef50610dda83
Source dataset
uspto-grants-2014_11
Patent number
US08883788B2

Reaction notes

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