Carbon Dioxide → HCID 13478464, compound

HRID 971492Notes

Reaction equation

HRID 971492 reaction equation
[CH3:1][C:2]1[CH:3]=[N:4][C:5]2[CH2:6][C:7]([CH3:13])([CH3:12])[CH2:8][CH2:9][C:10]=2[CH:11]=1.C([Li])CCC.[Li][CH:20]1C2N=CC(C)=CC=2CCC1(C)C.[C:33](=[O:35])=[O:34]>CCOCC.CCCCCC>[CH3:20][O:34][C:33]([CH:6]1[C:5]2[N:4]=[CH:3][C:2]([CH3:1])=[CH:11][C:10]=2[CH2:9][CH2:8][C:7]1([CH3:13])[CH3:12])=[O:35]

Participants

7

Reactant 4

HCID 280Carbon DioxideHCID 122782055,6,7,8-Tetrahydro-3,7,7-trimethylquinolineHCID 178418339ButyllithiumHCID 178506811HCID 178506811, compound

Product 1

HCID 13478464HCID 13478464, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8058HexaneSolvent

Procedure

3,7,7-Trimethyl-5,6,7,8-tetrahydroquinoline (17.5 g, 0.1 m) was dissolved in dry ether (200 ml.) and treated with a solution of n-butyl lithium in hexane (15% w/w solution, 56 ml.) under nitrogen. The reaction mixture containing 8-lithio-3,7,7-trimethyl-5,6,7,8-tetrahydroquinoline was allowed to stand at room temperature for 30 minutes and then treated with CO2 gas until the intense red colour was discharged. The reaction mixture was further treated as described in Example 36 of our copending U.S. Ser. No. 460,265 to give methyl-3,7,7-trimethyl-5,6,7,8-tetrahydroquinoline-8-carboxylate.

Workup

  1. additionThe reaction mixture was further treated

Sources & evidence

ORD record
ord-84e30269b6684e2f91674f135c21845d
Source dataset
uspto-grants-1979_07
Patent number
US04160094

Reaction notes

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