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

HRID 437074Notes

Reaction equation

HRID 437074 reaction equation
CC1C=CC2CCCCC=2[N:3]=1.C1([Li])C=CC=CC=1.C(=O)=O.[CH3:22][C:23]1[CH:32]=[CH:31][C:30]2[CH2:29][CH2:28][CH2:27][CH:26]([C:33]([O:35]C)=O)[C:25]=2[N:24]=1.N1C2CCCCC=2C=CC=1CC(OC)=O>>[CH3:22][C:23]1[CH:32]=[CH:31][C:30]2[CH2:29][CH2:28][CH2:27][CH:26]([C:33]([NH2:3])=[O:35])[C:25]=2[N:24]=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 coverted 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 coverted 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-9e90e13a63f94c929c58c6500edbc465
Source dataset
uspto-grants-1977_06
Patent number
US04029668

Reaction notes

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