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

HRID 1763233Notes

Reaction equation

HRID 1763233 reaction equation
[N+](C1C=C(S([O-])(=O)=O)C=CC=1)([O-])=O.[Na+].[OH:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[C:22]1[CH2:23][CH2:24][C:25](=[O:28])[NH:26][N:27]=1.[OH-].[Na+].C(O)(=O)C>O>[OH:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[C:22]1[CH:23]=[CH:24][C:25](=[O:28])[NH:26][N:27]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 31389Sodium 3-nitrobenzenesulfonateHCID 135731742HCID 135731742, compound

Product 1

HCID 30173466-(2-Hydroxyphenyl)-3(2H)-pyridazinoneYield 82.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Sodium 3-nitrobenzenesulphonate (2.96 g) and 6-(2-hydroxyphenyl)-4,5-dihydro-3(2H)pyridazinone (2.5 g) were added to a stirred solution of sodium hydroxide (1.31 g) in water (25 ml) and the mixture was heated under reflux for 2.5 hours. Acetic acid was added to the warm stirred solution until there was no further precipitation and the mixture was pH 9. The mixture was filtered to give 6-(2-hydroxyphenyl)-3(2H)-pyridazinone (2.05 g) m.p. 287°-292°. A sample recrystallised from 2-methoxyethanol had m.p. 295°-299°.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 2.5 hours
  3. customno further precipitation
  4. filtrationThe mixture was filtered

Sources & evidence

ORD record
ord-278fa023dbe04c6e99dd77003dd336e8
Source dataset
uspto-grants-1978_09
Patent number
US04111935

Reaction notes

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