Acetic Acid → 6-(2-Hydroxyphenyl)-3(2H)-pyridazinone

HRID 370752Notes

Reaction equation

HRID 370752 reaction equation
O[CH:2]([CH2:6][C:7](=O)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[OH:14])[C:3](O)=[O:4].[NH3:16].[NH2:17]N.C(O)(=O)C>O>[OH:14][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=1[C:7]1[CH:6]=[CH:2][C:3](=[O:4])[NH:16][N:17]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 222Ammonia2×HCID 9321HydrazineHCID 13778436HCID 13778436, compound

Product 1

HCID 30173466-(2-Hydroxyphenyl)-3(2H)-pyridazinoneYield 85%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred suspension of 2-hydroxy-4-oxo-4-(2-hydroxyphenyl)butyric acid in water was added ammonia until pH 7.0 was attained. Hydrazine was added slowly with the concurrent addition of sufficient glacial acetic acid to maintain a pH of 7.0. Steam heating was applied for 2 hours and during this time the pH of 7.0 was maintained by the addition of ammonia as necessary. The reaction mixture was allowed to cool to room temperature. The solid was filtered off, washed with water, 2-propanol and dried (MgSO4) to afford 6-(2-hydroxyphenyl)-3(2H)-pyridazinone (85%).

Workup

  1. temperatureto maintain a pH of 7.0
  2. temperatureSteam heating
  3. filtrationThe solid was filtered off
  4. washwashed with water, 2-propanol
  5. dry with materialdried (MgSO4)

Sources & evidence

ORD record
ord-caf4335781aa4d75bb4cdf7359c0a5b8
Source dataset
uspto-grants-1985_07
Patent number
US04528371

Reaction notes

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