Ammonium formate → HCID 11593771, compound

HRID 1357470Notes

Reaction equation

HRID 1357470 reaction equation
C([O:8][C:9]1[CH:10]=[CH:11][C:12]2[C:13]([N:25]=1)=[C:14]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[N:15]=[N:16][C:17]=2Cl)C1C=CC=CC=1.C([O-])=O.[NH4+]>[Pd].CC(O)C>[C:19]1([C:14]2[N:15]=[N:16][CH:17]=[C:12]3[CH:11]=[CH:10][C:9](=[O:8])[NH:25][C:13]=23)[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

5

Reactant 2

HCID 2723923Ammonium formate2×HCID 18186440HCID 18186440, compound

Product 1

HCID 11593771HCID 11593771, compoundYield 93.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 3776IsopropanolSolvent

Procedure

2-Benzyloxy-5-chloro-8-phenylpyrido[2,3-d]pyridazine (250 mg), ammonium formate (115 mg) and 10% palladium on carbon catalyst (50 mg) were stirred together at reflux in propan-2-ol (50 ml) for 30 min. More ammonium formate (45 mg) was added, and the mixture was stirred as before for a further 30 min, and was then allowed to cool to room temperature. The catalyst was removed by filtration, was washed thoroughly with methanol, and the filtrate was concentrated in vacuo to yield 8-phenyl-1H-pyrido[2,3-d]pyridazin-2-one as a white solid (150 mg). 1H NMR (400 MHz, CDCl3) δ6.98 (1H, d, J=9.4 Hz), 7.63 (3H, m), 7.69 (2H, m), 7.85 (1H, d, J=9.5 Hz), 8.88 (1H, br s), 9.23 (1H, s); MS (ES+) m/e 224 [MH]+.

Workup

  1. customThe catalyst was removed by filtration
  2. washwas washed thoroughly with methanol
  3. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-0d92bfd9aed24656998bae0a2253b2fe
Source dataset
uspto-grants-2003_07
Patent number
US06593325B1

Reaction notes

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