Hydrazine hydrate (1:1) → 5-phenylpyrido[2,3-d]pyridazin-8(7H)-one

HRID 1514391Notes

Reaction equation

HRID 1514391 reaction equation
[C:1]([C:9]1[C:10]([C:15]([OH:17])=O)=[N:11][CH:12]=[CH:13][CH:14]=1)(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.[NH2:19][NH2:20]>C(O)C>[C:2]1([C:1]2[C:9]3[CH:14]=[CH:13][CH:12]=[N:11][C:10]=3[C:15](=[O:17])[NH:19][N:20]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 7269413-Benzoylpyridine-2-carboxylic acid

Product 1

HCID 113335495-phenylpyrido[2,3-d]pyridazin-8(7H)-oneYield 71%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a round bottomed flask containing 3-benzoylpicolinic acid (2.00 g, 9 mmol) was added 50 mL of ethanol. Hydrazine hydrate (0.6 ml, 11 mmol) was added and the mixture was heated to reflux for 3 h. After cooling to rt, the solvent was removed in vacuo. The resulting yellow solid was recrystallized from 30 mL of boiling 1-propanol to afford 5-phenylpyrido[2,3-d]pyridazin-8(7H)-one 70 (1.4 g, 71% yield) as a white solid. 1H-NMR (400 MHz, CDCl3): δ 10.55 (br s, 1H), 9.16 (dd, J=8.6, 1.6 Hz, 1H), 7.73 (dd, J=8.6, 4.7 Hz, 1H), 7.56 (m, 5H).

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 3 h
  3. customthe solvent was removed in vacuo
  4. customThe resulting yellow solid was recrystallized from 30 mL of boiling 1-propanol

Sources & evidence

ORD record
ord-5e807fd2e2e846d6ac06177d350f8bf4
Source dataset
uspto-grants-2012_07
Patent number
US08222251B2

Reaction notes

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