Ammonia → 8-Quinolinecarboxamide, 5,6,7,8-tetrahydro-2-phenyl-

HRID 2083406Notes

Reaction equation

HRID 2083406 reaction equation
C[O:2][C:3]([CH:5]1[C:14]2[N:13]=[C:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH:11]=[CH:10][C:9]=2[CH2:8][CH2:7][CH2:6]1)=O.[NH3:21]>CO>[C:15]1([C:12]2[CH:11]=[CH:10][C:9]3[CH2:8][CH2:7][CH2:6][CH:5]([C:3]([NH2:21])=[O:2])[C:14]=3[N:13]=2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 12278956HCID 12278956, compound

Product 1

HCID 122789668-Quinolinecarboxamide, 5,6,7,8-tetrahydro-2-phenyl-

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
100 °C

Procedure

Methyl-2-phenyl-5,6,7,8-tetrahydroquinoline-8-carboxylate (4 g.) was dissolved in methanol previously saturated with ammonia (90 ml.) and heated in a bomb at 100° C for 4 days. Removal of the solvent in vacuo gave an oily solid which on recrystallisation from ethyl acetate gave the title compound as colourless needles (1.5 g.) mp 145° C. Found: C, 76.4; H, 6.5; N, 11.1% C16H16N2O requires: C, 76.2; H, 6.4; N, 11.1%.

Workup

  1. customRemoval of the solvent in vacuo
  2. customgave an oily solid which
  3. customon recrystallisation from ethyl acetate

Sources & evidence

ORD record
ord-65d107f5f3b842eba595f52686752c12
Source dataset
uspto-grants-1978_04
Patent number
US04085215

Reaction notes

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