Hydrochloric Acid → 4-Chloro-5-hydroxy-2-(phenylmethyl)-3(2H)-pyridazinone

HRID 2224267Notes

Reaction equation

HRID 2224267 reaction equation
[CH2:1]([N:8]1[C:13](=[O:14])[C:12]([Cl:15])=[C:11]([O:16]C)[CH:10]=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[K+].Cl>O>[CH2:1]([N:8]1[C:13](=[O:14])[C:12]([Cl:15])=[C:11]([OH:16])[CH:10]=[N:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 7370152-Benzyl-4-chloro-5-methoxypyridazin-3(2h)-one

Product 1

HCID 546831804-Chloro-5-hydroxy-2-(phenylmethyl)-3(2H)-pyridazinoneYield 98.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a suspension of 2-benzyl-4-chloro-5-methoxypyridazin-3(2H)-one (22.2 g, 87.47 mmol) in water (150.0 mL), potassium hydroxide (5.89 g) was added and the mixture was heated to reflux. After 3 h, the mixture was then cooled to room temperature and 6N aqueous hydrochloric acid was added and the pH of the solution was adjusted to 3.0. The precipitate was filtered, washed with water and dried under reduced pressure to give the title compound, 2-benzyl-4-chloro-5-hydroxypyridazin-3(2H)-one (20.45 g) as a white solid. HPLC: 2.40 min.

Workup

  1. additionwas added
  2. temperaturethe mixture was heated to reflux
  3. filtrationThe precipitate was filtered
  4. washwashed with water
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-3ad96037d2be475b97167c7736b3fdcd
Source dataset
uspto-grants-2008_05
Patent number
US07378418B2

Reaction notes

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