Acetonitrile → 3-[2-Cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl]-3-hydroxypropionitrile

HRID 1264168Notes

Reaction equation

HRID 1264168 reaction equation
[CH:1]1([C:4]2[C:13]([CH:14]=[O:15])=[C:12]([C:16]3[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=3)[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[N:5]=2)[CH2:3][CH2:2]1.[C:23](#[N:25])[CH3:24]>>[CH:1]1([C:4]2[C:13]([CH:14]=[CH:24][C:23]#[N:25])=[C:12]([C:16]3[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=3)[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[N:5]=2)[CH2:3][CH2:2]1.[CH:1]1([C:4]2[C:13]([CH:14]([OH:15])[CH2:24][C:23]#[N:25])=[C:12]([C:16]3[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=3)[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[N:5]=2)[CH2:2][CH2:3]1

Participants

4

Reactant 2

HCID 6342AcetonitrileHCID 99479742-Cyclopropyl-4-(4-fluorophenyl)-3-quinolinecarboxaldehyde

Product 2

HCID 114275473-[2-Cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl]-3-hydroxypropionitrileHCID 533950303-[2-Cyclopropyl-4-(4-fluorophenyl)-3-quinolyl]prop-2-enenitrile

Procedure

3-[2-Cyclopropyl-4-(4-fluorophenyl)-3-quinolyl]prop-2-enenitrile is prepared by reacting 2-cyclopropyl-4-(4-fluorophenyl)quinoline-3-carbaldehyde with acetonitrile in the presence of a base and then adding a dehydrating to the reaction mixture to conduct dehydration. Under ordinary conditions, novel 3-[2-cyclopropyl-4-(4-fluoro-phenyl)-quinolin-3-yl]-3-hydroxypropionitrile is formed as an intermediate in the above reaction. Incidentally, when the above reaction is conducted in an organic solvent, 3-[2-cyclopropyl-4-(4-fluorophenyl)-3-quinolyl]-prop-2-enenitrile is directly formed.

Workup

  1. additionadding a dehydrating to the reaction mixture

Sources & evidence

ORD record
ord-8354debb8dc34399b5c03322df838e54
Source dataset
uspto-grants-2003_04
Patent number
US06541636B2

Reaction notes

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