Ammonia → 5,6,7,8-Tetrahydroquinoline-8-carboxamide
Reaction equation
C[O:2][C:3]([CH:5]1[C:14]2[N:13]=[CH:12][CH:11]=[CH:10][C:9]=2[CH2:8][CH2:7][CH2:6]1)=O.[NH3:15]>CO>[N:13]1[C:14]2[CH:5]([C:3]([NH2:15])=[O:2])[CH2:6][CH2:7][CH2:8][C:9]=2[CH:10]=[CH:11][CH:12]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
Procedure
Methyl-5,6,7,8-tetrahydroquinoline-8-carboxylate (9 g.) was dissolved in methanol previously saturated with ammonia (270 ml.) and heated in a bomb at 100° C for 5 days. The solvent was removed and the residual oil triturated with hot petroleum ether (40°-60°). The resultant solid was filtered and then recrystallised from ethylacetate giving the title compound as colourless needles mpt. 132° C (5 g.). Found: C, 67.7; H, 7.1; N, 16.0% C10H12N2O requires: C, 68.1; H, 6.9; N, 15.9%.
Workup
- customThe solvent was removed
- customthe residual oil triturated with hot petroleum ether (40°-60°)
- filtrationThe resultant solid was filtered
- customrecrystallised from ethylacetate giving the title compound as colourless needles mpt
- custom132° C (5 g.)
Sources & evidence
- ORD record
- ord-b1a28d2b345a4a99a5a9d8f3f1e58ec2
- Source dataset
- uspto-grants-1977_02
- Patent number
- US04009169
Reaction notes
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