8-Quinolinecarboxamide, 5,6,7,8-tetrahydro-2-phenyl- → 8-Quinolinecarbonitrile, 5,6,7,8-tetrahydro-2-phenyl-
Reaction equation
[C:1]1([C:7]2[CH:16]=[CH:15][C:14]3[CH2:13][CH2:12][CH2:11][CH:10]([C:17]([NH2:19])=O)[C:9]=3[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>CN(C)P(=O)(N(C)C)N(C)C>[C:1]1([C:7]2[CH:16]=[CH:15][C:14]3[CH2:13][CH2:12][CH2:11][CH:10]([C:17]#[N:19])[C:9]=3[N:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1Participants
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 220 °C
Procedure
2-Phenyl-5,6,7,8-tetrahydroquinoline-8-carboxamide (6 g.) was dissolved in hexamethylphosphorictriamide (24 ml.) and the solution heated at 220° C for 2 hours. The cooled reaction mixture was poured onto water (50 ml.), extracted with chloroform (3 × 100 ml.) and the combined extracts washed with water (3 × 100 ml.), dried and evaporated to dryness. The residual oil was chromatographed on silica gel by elution with chloroform giving 2-phenyl-8-cyano-5,6,7,8-tetrahydroquinoline (2.5 g.) recrystallised from ether as colourless needles mpt. 100° C. Further elution with chloroform gave N,N-dimethyl-5,6,7,8-tetrahydroquinoline-8-carboxamide (1.1 g.) which recrystallised from ether as colourless needles mpt. 140° C. Found: C, 77.17; H, 7.22; N, 10.24%. C18H20N2O requires: C, 77.11; H, 7.19; N, 9.99%.
Workup
- customThe cooled reaction mixture
- additionwas poured onto water (50 ml.)
- extractionextracted with chloroform (3 × 100 ml.)
- washthe combined extracts washed with water (3 × 100 ml.)
- customdried
- customevaporated to dryness
- customThe residual oil was chromatographed on silica gel by elution with chloroform
Sources & evidence
- ORD record
- ord-9dc18b54a66345aa9845db9c04e9e4b0
- Source dataset
- uspto-grants-1977_02
- Patent number
- US04009169
Reaction notes
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