Carbon Dioxide → 2-Methyl-5,6,7,8-tetrahydroquinoline-8-carboxamide

HRID 596475Notes

Reaction equation

HRID 596475 reaction equation
CC1C=CC2CCCCC=2[N:3]=1.C1([Li])C=CC=CC=1.C(=O)=O.C[O:23][C:24]([CH:26]1[C:35]2[N:34]=[C:33]([CH3:36])[CH:32]=[CH:31][C:30]=2[CH2:29][CH2:28][CH2:27]1)=O.N1C2CCCCC=2C=CC=1CC(OC)=O>>[CH3:36][C:33]1[CH:32]=[CH:31][C:30]2[CH2:29][CH2:28][CH2:27][CH:26]([C:24]([NH2:3])=[O:23])[C:35]=2[N:34]=1

Participants

6

Reactant 5

HCID 280Carbon DioxideHCID 122294205,6,7,8-Tetrahydro-2-methylquinolineHCID 12278958Methyl-2-methyl-5,6,7,8-tetrahydroquinoline-8-carboxylateHCID 20358396Methyl 5,6,7,8-tetrahydroquinoline-2-acetateHCID 178506676HCID 178506676, compound

Product 1

HCID 122789682-Methyl-5,6,7,8-tetrahydroquinoline-8-carboxamideYield 30%

Procedure

Reaction of 2-methyl-5,6,7,8-tetrahydroquinoline with phenyl lithium and carbon dioxide followed by esterification according to the general method described in Examples 1B and 6B gave an inseparable mixture of methyl-2-methyl-5,6,7,8-tetrahydroquinoline-8-carboxylate and methyl 5,6,7,8-tetrahydroquinoline-2-acetate which was converted without purification to a mixture of 2-methyl-5,6,7,8-tetrahydroquinoline-8-carboxamide and 5,6,7,8-tetrahydroquinoline-2-acetamide by reaction with ammonia using the method described in Example 2. Fractional recrystallisation from diisopropyl ether gave the title compound as colourless needles m.p. 114° (overall yield 30%) (Found: C, 69.31, H, 7.45, N, 14.7, C11H14N2O requires: C, 69.45, H, 7.42; N, 14.72%).

Workup

  1. customgave
  2. customwas converted without purification to a mixture of 2-methyl-5,6,7,8-tetrahydroquinoline-8-carboxamide and 5,6,7,8-tetrahydroquinoline-2-acetamide by reaction with ammonia using the method
  3. customFractional recrystallisation from diisopropyl ether

Sources & evidence

ORD record
ord-7ee46ff3292c496996f010d2b95e7b64
Source dataset
uspto-grants-1977_03
Patent number
US04011225

Reaction notes

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