Carbon Dioxide → 8-Quinolinecarboxylic acid, 5,6,7,8-tetrahydro-3-methyl-, methyl ester

HRID 971499Notes

Reaction equation

HRID 971499 reaction equation
[CH3:1]C1C=NC2CCCCC=2C=1.C[Li].[Li]C1C2N=CC(C)=CC=2CCC1.C(=O)=O.[Li+].[CH3:30][C:31]1[CH:32]=[N:33][C:34]2[CH:35]([C:41]([O-:43])=[O:42])[CH2:36][CH2:37][CH2:38][C:39]=2[CH:40]=1>CCOCC>[CH3:1][O:42][C:41]([CH:35]1[C:34]2[N:33]=[CH:32][C:31]([CH3:30])=[CH:40][C:39]=2[CH2:38][CH2:37][CH2:36]1)=[O:43]

Participants

7

Reactant 5

HCID 280Carbon DioxideHCID 1200283-Methyl-5,6,7,8-tetrahydroquinolineHCID 70603145HCID 70603145, compoundHCID 178418348HCID 178418348, compoundHCID 178506833HCID 178506833, compound

Product 1

HCID 122789608-Quinolinecarboxylic acid, 5,6,7,8-tetrahydro-3-methyl-, methyl ester

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 3-methyl-5,6,7,8-tetrahydroquinoline (10 g) in anhydrous ether (50 ml) was added dropwise with stirring under nitrogen a 1.67 molar solution of methyllithium (40 ml.). The stirring was continued for 1/2 hour then the dark red solution of 8-lithio-3-methyl-5,6,7,8-tetrahydroquinoline was treated with a brisk stream of CO2 gas until the suspension became pale yellow. The resulting 3-methyl-5,6,7,8-tetrahydroquinoline-8-carboxylic acid lithium salt was processed in the manner described in copending application U.S. Ser. No. 460,265 to give methyl-3-methyl-5,6,7,8-tetrahydroquinoline-8-carboxylate.

Sources & evidence

ORD record
ord-5434fa057ddb4501b4b884bf55911abe
Source dataset
uspto-grants-1979_07
Patent number
US04160094

Reaction notes

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