3-Methyl-5,6,7,8-tetrahydroquinoline → HCID 178506833, compound

HRID 971491Notes

Reaction equation

HRID 971491 reaction equation
[CH2:1]([Li:5])[CH2:2][CH2:3][CH3:4].[CH3:6][C:7]1[CH:8]=[N:9][C:10]2CCCC[C:15]=2[CH:16]=1>CCCCCC.CCOCC>[Li:5][CH:1]1[C:10]2[N:9]=[CH:8][C:7]([CH3:6])=[CH:16][C:15]=2[CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 1200283-Methyl-5,6,7,8-tetrahydroquinolineHCID 178418339Butyllithium

Product 1

HCID 178506833HCID 178506833, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8058HexaneSolvent

Procedure

A solution of 15% w/w n-butyl lithium in hexane (51 ml.) ca. 0.12 m) was added portionwise to a solution of 3-methyl-5,6,7,8-tetrahydroquinoline (14.7 g., 0.1 m) in ether (100 ml.) and the mixture allowed to stand at room temperature for 1 hour to form 8-lithio-3-methyl-5,6,7,8-tetrahydroquinoline. The solution was then added dropwise to a cooled, stirred solution of methylchloroformate (9.45 g., 0.1 m) in ether (100 ml.). The mixture was further treated as described in Example 25 of copending U.S. Ser. No. 460,265 to give methyl-3-methyl-5,6,7,8-tetrahydroquinoline-8-carboxylate.

Sources & evidence

ORD record
ord-ddf374d0c43f45458e3b0725f3508289
Source dataset
uspto-grants-1979_07
Patent number
US04160094

Reaction notes

Loading…