Water → 5,6-bis(4-Methoxyphenyl)-4-cyano-2-cyclopropylmethyl-2H-pyridazin-3-one

HRID 1840262Notes

Reaction equation

Cl[CH2:2][CH:3]1[CH2:5][CH2:4]1.[CH3:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[C:19]([C:20]3[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=3)=[N:18][NH:17][C:16](=[O:28])[C:15]=2[C:29]#[N:30])=[CH:10][CH:9]=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[CH3:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[C:19]([C:20]3[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=3)=[N:18][N:17]([CH2:2][CH:3]3[CH2:5][CH2:4]3)[C:16](=[O:28])[C:15]=2[C:29]#[N:30])=[CH:10][CH:9]=1

Participants

Conditions

Temperature: 80 °C

Procedure

(Chloromethyl)cyclopropane (0.6 ml, 6.36 mmol) was added to a solution of 5,6-bis(4-methoxyphenyl)-4-cyano-2H-pyridazin-3-one (1.71 g, 5.10 mmol) and potassium carbonate (2.02 g, 14.62 mmol) in N,N-dimethylformamide (5 ml), followed by stirring at a bath temperature of 80° C. for 6 hours. Water was then added to the reaction mixture, followed by extraction with ethyl acetate (300 ml). The organic layer was washed with water and a saturated aqueous solution of sodium chloride (brine), successively, and was then dried over anhydrous sodium sulfate. The solvent was distilled off, whereby the title compound (1.413 g, 71.5%) was obtained as yellow crystals.

Workup

extractionfollowed by extraction with ethyl acetate (300 ml)
washThe organic layer was washed with water
dry with materiala saturated aqueous solution of sodium chloride (brine), successively, and was then dried over anhydrous sodium sulfate
distillationThe solvent was distilled off

Sources & evidence

ORD record: ord-1d37119ed04646c7a240cbfaf616a489
Source dataset: uspto-grants-2004_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06680316B1

Reaction notes

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