Carbon Dioxide → HCID 21314201, compound

HRID 971493Notes

Reaction equation

HRID 971493 reaction equation
[CH3:1][C:2]1[C:11]2[CH2:10][CH2:9][CH2:8][CH2:7][C:6]=2[N:5]=[CH:4][CH:3]=1.C([Li])CCC.CCCCCC.[Li][CH:24]1C2N=CC=C(C)C=2CCC1.[C:35](=[O:37])=[O:36].Cl>C1C=CC=CC=1>[CH3:24][O:36][C:35]([CH:7]1[C:6]2[N:5]=[CH:4][CH:3]=[C:2]([CH3:1])[C:11]=2[CH2:10][CH2:9][CH2:8]1)=[O:37]

Participants

8

Reactant 6

HCID 280Carbon DioxideHCID 313Hydrochloric AcidHCID 8058HexaneHCID 1856675,6,7,8-Tetrahydro-4-methylquinolineHCID 178418339ButyllithiumHCID 178506834HCID 178506834, compound

Product 1

HCID 21314201HCID 21314201, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of 4-methyl-5,6,7,8-tetrahydroquinoline (5.83 g., 0.04 mole) in dry benzene (40 ml.) was cooled to 0° and to the stirred solution was added dropwise a 15% w/w solution of butyl lithium in hexane (17.5 ml., 0.04 mole) under an atmosphere of nitrogen. The red reaction mixture of 8-lithio-4-methyl-5,6,7,8-tetrahydroquinoline was stirred at 0° for a further 30 minutes. It can then be treated with carbon dioxide followed by methanolic HCl to obtain methyl-4-methyl-5,6,7,8-tetrahydroquinoline-8-carboxylate which can be converted to 4-methyl-5,6,7,8-tetrahydroquinoline-8-thiocarboxamide by the procedures described in copending U.S. Ser. No. 460,265.

Sources & evidence

ORD record
ord-3223608d9b004caebe5a908e50fd5998
Source dataset
uspto-grants-1979_07
Patent number
US04160094

Reaction notes

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