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

HRID 437070Notes

Reaction equation

HRID 437070 reaction equation
[N:1]1[C:10]2[CH:9]([C:11]([O:13]C)=O)[CH2:8][CH2:7][CH2:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.[NH3:15]>CO>[N:1]1[C:10]2[CH:9]([C:11]([NH2:15])=[O:13])[CH2:8][CH2:7][CH2:6][C:5]=2[CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 12278957Methyl 5,6,7,8-tetrahydroquinoline-8-carboxylate

Product 1

HCID 122789675,6,7,8-Tetrahydroquinoline-8-carboxamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

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 ethyl acetate 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

  1. customThe solvent was removed
  2. customthe residual oil triturated with hot petroleum ether (40°-60°)
  3. filtrationThe resultant solid was filtered
  4. customrecrystallised from ethyl acetate giving the title compound as colourless needles mpt
  5. custom132° C. (5 g.)

Sources & evidence

ORD record
ord-909459826dda4a479ab8022363375df2
Source dataset
uspto-grants-1977_06
Patent number
US04029668

Reaction notes

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