2-Fluoro-5-formylbenzonitrile → 4-(3-Cyano-4-fluorophenyl)-1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarbonitrile

HRID 218476

Reaktionsgleichung

[F:1][C:2]1[CH:9]=[CH:8][C:7]([CH:10]=O)=[CH:6][C:3]=1[C:4]#[N:5].[NH2:12]/[C:13](/[CH3:17])=[CH:14]\[C:15]#[N:16]>C(O)(=O)C>[C:4]([C:3]1[CH:6]=[C:7]([CH:10]2[C:14]([C:15]#[N:16])=[C:13]([CH3:17])[NH:12][C:2]([CH3:9])=[C:3]2[C:4]#[N:5])[CH:8]=[CH:9][C:2]=1[F:1])#[N:5]

Komponenten

Reaktionsbedingungen

Temperatur: 90 °C

Versuchsvorschrift

2-Fluoro-5-formylbenzonitrile (30 g, 201.17 mmol) and 3-aminocrotononitrile (35.01 g, 431.63 mmol) were dissolved in acetic acid and heated to 90° C. After 4 hr, the reaction mixture was cooled to rt, concentrated, neutralized with a saturated solution of sodium bicarbonate, and extracted with ethyl acetate. The organic extracts were dried over sodium sulfate and concentrated. The solid were dissolved into ethyl acetate, and hexane was added. The solid precipitated, and was filtered to afford 4-(3-cyano-4-fluorophenyl)-1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarbonitrile (44.9 g, 80.2%) as a pale yellow solid. 1H-NMR (400 MHZ, DMSO-D6): δ=9.61 (br. s, 1H), 7.97 (dd, 1H), 7.48 (dd, 1H), 7.35 (dd, 1H), 4.64 (s, 1H), 2.01 (s, 6H) ppm.

Aufarbeitung

temperaturethe reaction mixture was cooled to rt
concentrationconcentrated
extractionextracted with ethyl acetate
dry with materialThe organic extracts were dried over sodium sulfate
concentrationconcentrated
dissolutionThe solid were dissolved into ethyl acetate, and hexane
additionwas added
customThe solid precipitated
filtrationwas filtered

Quellen und Nachweise

ORD-Eintrag: ord-bb2ef7ff04d641a5ba61d78b182bda24
Quelldatensatz: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08198456B2

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