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

HRID 861951Notes

Reaction equation

HRID 861951 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](OC)=[O:16])=[CH:13][CH:12]=[CH:11][N:10]=1)=O)([O-:3])=[O:2].O.[NH2:23][NH2:24].C(OCC)(=O)C>C(O)C>[N+:1]([C:4]1[CH:5]=[C:6]([C:7]2[C:9]3[N:10]=[CH:11][CH:12]=[CH:13][C:14]=3[C:15](=[O:16])[NH:24][N:23]=2)[CH:19]=[CH:20][CH:21]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 24654Hydrazine hydrate (1:1)HCID 197007162-(3-Nitrobenzoyl)-3-methoxycarbonylpyridine

Product 1

HCID 197007208-(3-Nitrophenyl) pyrido[2,3-d]pyridazin-5-oneYield 108.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2-(3-nitrobenzoyl)-3-methoxycarbonylpyridine (0.58 g, 2 mmoles) dissolved in ethanol (50 ml), was added hydrazine monohydrate (0.25 ml, 5.1 mmoles). The mixture was refluxed for 4 hours, cooled and ethyl acetate (50 ml) was added. The solid material was collected and dried, yielding 0.58 g of 8-(3-nitrophenyl)-pyrido[2,3-d]pyridazin-5-one, mp 302° C.

Workup

  1. temperatureThe mixture was refluxed for 4 hours
  2. temperaturecooled
  3. customThe solid material was collected
  4. customdried

Sources & evidence

ORD record
ord-9260ee1f34c94541af80f0290ed706c5
Source dataset
uspto-grants-1998_02
Patent number
US05716954

Reaction notes

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