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

HRID 971489Notes

Reaction equation

HRID 971489 reaction equation
[CH3:1][C:2]1[CH:3]=[N:4][C:5]2[CH2:6][CH2:7][CH2:8][CH2:9][C:10]=2[CH:11]=1.C([Li])CCC.[Li][CH:18]1C2N=CC(C)=CC=2CCC1.[C:29](=[O:31])=[O:30]>CCOCC>[CH3:18][O:30][C:29]([CH:6]1[C:5]2[N:4]=[CH:3][C:2]([CH3:1])=[CH:11][C:10]=2[CH2:9][CH2:8][CH2:7]1)=[O:31]

Participants

6

Reactant 4

HCID 280Carbon DioxideHCID 1200283-Methyl-5,6,7,8-tetrahydroquinolineHCID 178418339ButyllithiumHCID 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

A stirred solution of 3-methyl-5,6,7,8-tetrahydroquinoline (147 g., 1 m) in dry ether (700 ml.) was treated with a freshly prepared solution of butyl lithium (860 ml. of a 1.4 M solution i.e. 1.2 m) under nitrogen. The reaction mixture was stirred for an additional 15 min. The resulting 8-lithio-3-methyl-5,6,7,8-tetrahydroquinoline was treated in situ with a slow stream of dry CO2 gas which was bubbled into the reaction mixture until it became colourless. The reaction mixture was processed as described in Example 19 of our copending U.S. Ser. No. 460,265 to give methyl-3-methyl-5,6,7,8-tetrahydroquinoline-8-carboxylate.

Workup

  1. customwas bubbled into the reaction mixture until it

Sources & evidence

ORD record
ord-49fdf3e1b20847bfba5b2f07de507f82
Source dataset
uspto-grants-1979_07
Patent number
US04160094

Reaction notes

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