3-Methyl-8-(trimethylsilyl)-5,6,7,8-tetrahydroquinoline → HCID 178506786, compound

HRID 482974Notes

Reaction equation

HRID 482974 reaction equation
C([Li:5])CCC.[CH3:6][Si:7]([CH3:20])([CH3:19])[CH:8]1[C:17]2[N:16]=[CH:15][C:14]([CH3:18])=[CH:13][C:12]=2[CH2:11][CH2:10][CH2:9]1>CCCCCC.C1COCC1>[Li:5][C:8]1([Si:7]([CH3:19])([CH3:20])[CH3:6])[C:17]2[N:16]=[CH:15][C:14]([CH3:18])=[CH:13][C:12]=2[CH2:11][CH2:10][CH2:9]1

Participants

5

Reactant 2

HCID 202445183-Methyl-8-(trimethylsilyl)-5,6,7,8-tetrahydroquinolineHCID 178418339Butyllithium

Product 1

HCID 178506786HCID 178506786, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent2×

Procedure

A mixture of a 1.55 molar solution of butyl lithium in hexane (6.45 ml, 1O mM) and THF (10 ml) maintained below 10° was treated with a solution of 5,6,7,8-tetrahydro-8-trimethylsilyl-3-methylquinoline (2.2 g, 10 mM) in THF (1O ml) to obtain 5,6,7,8-tetrahydro- -8-lithio-8-trimethylsilyl-3-methylquinoline. After 0.5 hour a 22% solution of t-butyldimethylsilyl isothiocyanate in benzene (6.9 g, 1O mM) was added dropwise. After 0.5 hour the reaction mixture was quenched with 2N hydrochloric acid (25 ml) and after 1 hour the aqueous layer was separated, basified (to pH9) and extracted with dichloromethane (2×50 ml). The organic extracts were dried and evaporated to give the title thioamide (2.1 g, c 100%). Recrystallisation from benzene gave analytically pure material (1.9 g, 88%) m.p. 153°, identical to authentic material (Found: C63.7; H,6.9; N,13.4% C11H14N2S requires: C64.0; H,6.8; N,13.6%).

Workup

  1. temperaturemaintained below 10°

Sources & evidence

ORD record
ord-fa7aa15cdba741379341a467d276c30b
Source dataset
uspto-grants-1986_03
Patent number
US04577022

Reaction notes

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