Ammonia → 6-(2-Hydroxyphenyl)-3(2H)-pyridazinone

HRID 370753Notes

Reaction equation

HRID 370753 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].Cl.[NH2:17][NH2:18].N>O.C(O)(=O)C.C(N(CC)CC)C>[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:17][N:18]=1

Participants

8

Reactant 4

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 9321HydrazineHCID 13778436HCID 13778436, compound

Product 1

HCID 30173466-(2-Hydroxyphenyl)-3(2H)-pyridazinoneYield 78.3%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 8471TriethylamineSolvent

Procedure

To a stirred suspension of 2-hydroxy-4-oxo-4-(2-hydroxyphenyl)butyric acid (0.025M) in water (20 ml) was added triethylamine (3.3 ml), taking the pH to 9.5, followed by concentrated hydrochloric acid (2.5 ml) to take the pH to 4. Hydrazine (0.05M) 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 to afford 6-(2-hydroxyphenyl)-3(2H)-pyridazinone (78.3%).

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. customdried

Sources & evidence

ORD record
ord-77b26cc6ff1148b685509d4ad536726f
Source dataset
uspto-grants-1985_07
Patent number
US04528371

Reaction notes

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