Hydrazine, (phenylmethyl)-, hydrochloride (1:1) → 6-Benzyl-8-(3-nitrophenyl)pyrido[2,3-d]pyridazin-5-one

HRID 861953Notes

Reaction equation

[N+:1]([C:4]1[CH:5]=[C:6]([CH:19]=[CH:20][CH:21]=1)[C:7]([C:9]1[C:14]([C:15]([O:17]C)=O)=[CH:13][CH:12]=[CH:11][N:10]=1)=O)([O-:3])=[O:2].Cl.[CH2:23]([NH:30][NH2:31])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>C(O)C>[CH2:23]([N:30]1[C:15](=[O:17])[C:14]2[CH:13]=[CH:12][CH:11]=[N:10][C:9]=2[C:7]([C:6]2[CH:19]=[CH:20][CH:21]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)=[N:31]1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

Conditions

Temperature: 85 °C

Procedure

To a solution of 2-(3-nitrobenzoyl)-3-methoxycarbonylpyridine (0.20 g, 0.75 mmoles) dissolved in ethanol (50 ml), was added benzylhydrazine hydrochloride (0.36 g, 1.86 mmoles). The mixture was heated to 85° C. for 144 hours. The mixture was purified by chromatography yielding 0.11 g of 6-benzyl-8-(3-nitrophenyl)pyrido[2,3-d]pyridazin-5-one (41%), mp 132° C.

Workup

customThe mixture was purified by chromatography

Sources & evidence

ORD record: ord-bd4105b67b4e4ff6b55839b5ca503038
Source dataset: uspto-grants-1998_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05716954

Reaction notes

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