Hydrazine → 8-(3-Nitrophenyl) pyrido[2,3-d]pyridazin-5-one

HRID 861970Notes

Reaction equation

HRID 861970 reaction equation
O[C:2]1([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([N+:18]([O-:20])=[O:19])[CH:13]=2)[C:6]2=[N:7][CH:8]=[CH:9][CH:10]=[C:5]2[C:4](=O)[O:3]1.[NH2:21][NH2:22]>CO>[N+:18]([C:14]1[CH:13]=[C:12]([C:2]2[C:6]3[N:7]=[CH:8][CH:9]=[CH:10][C:5]=3[C:4](=[O:3])[NH:22][N:21]=2)[CH:17]=[CH:16][CH:15]=1)([O-:20])=[O:19]

Participants

4

Reactant 2

HCID 9321HydrazineHCID 197008147-hydroxy-7-(3-nitrophenyl)-7H-furo[3,4-b]pyridin-5-one

Product 1

HCID 197007208-(3-Nitrophenyl) pyrido[2,3-d]pyridazin-5-one

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

7-Hydroxy-7-(3-nitrophenyl)-7H-furo[3,4-b]pyridin-5-one (38.65 g, 142 mmoles) was mixed with 800 mL of methanol. To this mixture was added 35 mL of anhydrous hydrazine. The resulting solution was then heated under reflux for 5 hours. After 17 hours of aging at room temperature the product was isolated by filtration. The crystalline mass was washed twice with methanol (250 mL) and dried, yielding 25.6 g of 8-(3-nitrophenyl)- pyrido[2,3-d]pyridazin-5-one.

Workup

  1. temperatureThe resulting solution was then heated
  2. temperatureunder reflux for 5 hours
  3. customthe product was isolated by filtration
  4. washThe crystalline mass was washed twice with methanol (250 mL)
  5. customdried

Sources & evidence

ORD record
ord-ef522fb6b8344cb282748fd42975163c
Source dataset
uspto-grants-1998_02
Patent number
US05716954

Reaction notes

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