Hydrochloric Acid → 6-(Furan-2-yl)-2-oxo-1,2-dihydropyridine-3-carbonitrile

HRID 353213Notes

Reaction equation

CN(C)[CH:3]=[CH:4][C:5]([C:7]1[O:8][CH:9]=[CH:10][CH:11]=1)=O.[C:13]([CH2:15][C:16]([NH2:18])=[O:17])#[N:14].C(=O)([O-])[O-].[K+].[K+].Cl>CS(C)=O.O>[O:8]1[CH:9]=[CH:10][CH:11]=[C:7]1[C:5]1[NH:18][C:16](=[O:17])[C:15]([C:13]#[N:14])=[CH:3][CH:4]=1

Participants

Conditions

Temperature: 130 °C

Procedure

A suspension of 3-(dimethylamino)-1-(2-furyl)-2-propen-1-one (15.0 g, 90.9 mmol), 2-cyanoacetamide (8.5 g, 101 mmol) and potassium carbonate (38.0 g, 275 mmol) in dimethyl sulfoxide (80 ml) was stirred at 120 to 140° C. for 21 hours. After cooling as it was, the reaction mixture was diluted with water. After adjusting to pH 3 with conc. hydrochloric acid, the resulting solid was collected by filtration and washed with water, to give the title compound (13.0 g, 77%) as a brown solid.

Workup

temperatureAfter cooling as it
filtrationthe resulting solid was collected by filtration
washwashed with water

Sources & evidence

ORD record: ord-e778b8b6f0414bec9b84149b89bbbd63
Source dataset: uspto-grants-2004_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06750232B2

Reaction notes

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