Diethyl Ether → 4-Hydroxy-2-methyl-6-oxo-1,6-dihydropyridine-3-carbonitrile

HRID 590817Notes

Reaction equation

[NH2:1]/[C:2](/[CH3:6])=[CH:3]/[C:4]#[N:5].[C:7](OC1C(Cl)=CC(Cl)=CC=1Cl)(=[O:21])[CH2:8][C:9](OC1C(Cl)=CC(Cl)=CC=1Cl)=[O:10].CCOCC>COCCOCCOC>[OH:21][C:7]1[C:3]([C:4]#[N:5])=[C:2]([CH3:6])[NH:1][C:9](=[O:10])[CH:8]=1

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of (E)-3-aminobut-2-enenitrile (9.7 g, 118 mmol) and bis(2,4,6-trichlorophenyl) malonate (58.4 g, 126 mmol) in diglyme (120 ml) was heated to 120° C. for 2.5 hr. The mixture was cooled to RT and poured into Et2O and filtered to collect the precipitate. The precipitate was washed with Et20 to obtain 4-hydroxy-2-methyl-6-oxo-1,6-dihydropyridine-3-carbonitrile. MS ESI calc'd. for C7H7N2O2 [M+H]+ 151. found 151.

Workup

temperatureThe mixture was cooled to RT
filtrationfiltered
customto collect the precipitate
washThe precipitate was washed with Et20

Sources & evidence

ORD record: ord-9d01770b36344ffb8bf4b521c1a2559b
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09233979B2

Reaction notes

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