Ammonia → 5,6,7,8-Tetrahydroquinoline-8-carboxamide

HRID 437459Notes

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]=1

Participants

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, 6.8.1; 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.) Found

Sources & evidence

ORD record: ord-7175ec383a2a4dab948fe111bfc9de18
Source dataset: uspto-grants-1977_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04031102

Reaction notes

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