Phosphorus sulfide (P2S5) → 8-Quinolinecarbonitrile, 5,6,7,8-tetrahydro-2-phenyl-

HRID 436470Notes

Reaction equation

HRID 436470 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.P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=S>N1C=CC=CC=1>[C:17]([CH:10]1[C:9]2[N:8]=[C:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[CH:16]=[CH:15][C:14]=2[CH2:13][CH2:12][CH2:11]1)#[N:19]

Participants

4

Reactant 2

HCID 14817Phosphorus sulfide (P2S5)HCID 122789668-Quinolinecarboxamide, 5,6,7,8-tetrahydro-2-phenyl-

Product 1

HCID 122789758-Quinolinecarbonitrile, 5,6,7,8-tetrahydro-2-phenyl-Yield 16.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

2-Phenyl-5,6,7,8-tetrahydroquinoline-8-carboxamide (8 g.) was dissolved in pyridine (20 ml.), treated with P2S5 (5.2 g.) and the mixture heated at reflux temperature for 30 minutes. The solvent was removed in vacuo and the residual oil dissolved in dilute HCl, washed with ether (2 × 50 ml.) and the washings discarded. The aqueous solution was made basic, extracted into chloroform (3 × 50 ml.) and the combined extracts dried and evaporated to dryness. The residual oil was chromatographed on silica gel by elution with chloroform giving 8-cyano-2-phenyl-5,6,7,8-tetrahydroquinoline (1.2 g.) as colourless needles from ether mpt. 100° C. Found: C, 82.0; H, 6.2; N, 11.7% C16H14N2 requires: C, 82.0; H, 6.0; N, 11.9%. Further elution with chloroform gave the title compound (1.1 g.) as colourless needles from ether mpt. 154° C. Found: C, 71.8; H, 6.1; N, 10.2 %, C16H16N2S requires: C, 71.6; H, 6.0; N, 10.4%.

Workup

  1. temperaturethe mixture heated
  2. temperatureat reflux temperature for 30 minutes
  3. customThe solvent was removed in vacuo
  4. dissolutionthe residual oil dissolved in dilute HCl
  5. washwashed with ether (2 × 50 ml.)
  6. extractionextracted into chloroform (3 × 50 ml.)
  7. customthe combined extracts dried
  8. customevaporated to dryness
  9. customThe residual oil was chromatographed on silica gel by elution with chloroform

Sources & evidence

ORD record
ord-fb86615940f44d1089477f97e5b96c45
Source dataset
uspto-grants-1977_02
Patent number
US04009169

Reaction notes

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