Water → 4-(2,6-Diethyl-4-methylphenyl)-5-hydroxy-2,6-dimethyl-3(2H)-pyridazinone

HRID 335460Notes

Reaction equation

[CH2:1]([C:3]1[CH:8]=[C:7]([CH3:9])[CH:6]=[C:5]([CH2:10][CH3:11])[C:4]=1[C:12]1[C:13](=[O:24])[N:14]([CH3:23])[N:15]=[C:16]([CH3:22])[C:17]=1S(C)(=O)=O)[CH3:2].CN1CCCC1=[O:31].[OH-].[Na+].O>C1(C)C=CC=CC=1>[CH2:1]([C:3]1[CH:8]=[C:7]([CH3:9])[CH:6]=[C:5]([CH2:10][CH3:11])[C:4]=1[C:12]1[C:13](=[O:24])[N:14]([CH3:23])[N:15]=[C:16]([CH3:22])[C:17]=1[OH:31])[CH3:2]

Participants

Conditions

Temperature: 70 °C

Procedure

To a 25 mL volume three-necked flask, 4-(2,6-diethyl-4-methylphenyl)-2,6-dimethyl-5-methylsulfonyl-2,3-dihydro-3-pyridazinone ((2-34)-(1)-39) (1.71 g), N-methyl-2-pyrrolidone (3.1 ml), and 27 w/w % of aqueous sodium hydroxide solution (2.99 g) were added, and stirred at 70° C. for 6 hours. To the mixture was added water (4.0 ml) and toluene (4.6 ml), and then the organic layer was removed. To the resulting aqueous layer, 35 w/w % of hydrochloric acid was added to adjust to pH to less than 1. The precipitated crystals were collected by filtration, washed with water, and dried under reduced pressure to give 1.23 g of 4-(2,6-diethyl-4-methylphenyl)-5-hydroxy-2,6-dimethyl-2,3-dihydro-3-pyridazinone ((1-4)-(1)-39).

Workup

customthe organic layer was removed
additionTo the resulting aqueous layer, 35 w/w % of hydrochloric acid was added
filtrationThe precipitated crystals were collected by filtration
washwashed with water
customdried under reduced pressure

Sources & evidence

ORD record: ord-1997e5da31c3409bb3dfb953d32c15f0
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08884010B2

Reaction notes

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