Water → 8-Hydroxy-7-phenyl-2,3-dihydropyrido[3,4-d]pyridazine-1,4-dione

HRID 37460Notes

Reaction equation

HRID 37460 reaction equation
[O:1]1[CH:5]2[CH:6]([C:12](OC)=[O:13])[CH:7]([C:8](OC)=[O:9])[C:2]1(OCC)[C:3]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[N:4]2.O.[NH2:26][NH2:27].O>C(O)(=O)C>[OH:1][C:2]1[C:7]2[C:8](=[O:9])[NH:27][NH:26][C:12](=[O:13])[C:6]=2[CH:5]=[N:4][C:3]=1[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 962WaterHCID 24654Hydrazine hydrate (1:1)HCID 199355783,6-Epoxy-3-ethoxy-4,5-dimethoxycarbonyl-2-phenyl-3,4,5,6-tetrahydropyridine

Product 1

HCID 123246328-Hydroxy-7-phenyl-2,3-dihydropyrido[3,4-d]pyridazine-1,4-dione

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

3,6-Epoxy-3-ethoxy-4,5-dimethoxycarbonyl-2-phenyl-3,4,5,6-tetrahydropyridine (500 mg; 1.5 mmol) was added to hydrazine monohydrate (5 ml), and the mixture was heated in a stream of nitrogen at 100° C. for 1 hour. Under ice-cooling, water was added to reaction mixture, and the mixture was neutralized with acetic acid. The resulting yellow crystalline precipitate was recovered by filtration. Yield: 210 mg (55.0%).

Workup

  1. temperatureUnder ice-cooling
  2. filtrationThe resulting yellow crystalline precipitate was recovered by filtration

Sources & evidence

ORD record
ord-d9842279ec7b42979543382210428482
Source dataset
uspto-grants-1995_05
Patent number
US05420275

Reaction notes

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