Hydrochloric Acid → Z-5,6,7,8-Tetrahydro-4-methyl-8-(1-(4-methylphenyl)ethylidene)quinoline

HRID 235042Notes

Reaction equation

HRID 235042 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.[CH2:12]([Li])[CH2:13][CH2:14][CH3:15].C[Si](Cl)(C)C.Cl>O1CCCC1>[CH3:1][C:2]1[C:11]2[CH2:10][CH2:9][CH2:8]/[C:7](=[C:14](/[C:13]3[CH:12]=[CH:1][C:2]([CH3:11])=[CH:3][CH:4]=3)\[CH3:15])/[C:6]=2[N:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6397ChlorotrimethylsilaneHCID 1856675,6,7,8-Tetrahydro-4-methylquinolineHCID 178418339Butyllithium2×

Product 1

HCID 10467950Z-5,6,7,8-Tetrahydro-4-methyl-8-(1-(4-methylphenyl)ethylidene)quinoline

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent4×

Conditions

Temperature
0 °C

Procedure

5,6,7,8-Tetrahydro-4-methylquinoline (7.5 g) in tetrahydrofuran (THF) (25 ml) was added to a solution of n-butyl lithium (1.37M, 37 ml) in THF (40 ml) maintained at 0° C. After 30 minutes the solution was blown over with nitrogen onto a solution of trimethylsilyl chloride (5.6 g) in THF (25 ml) at 0° C. Further n-butyl lithium (1.37M, 37 ml) was added and after 30 minutes the reaction mixture was blown over with nitrogen onto 4-methylacetophenone (15 g) in THF (25 ml) at 0° C. After 10 minutes 2M HCl (150 ml) was added.

Sources & evidence

ORD record
ord-8aa5af5557b5489bbb5d5c0bd70aa14d
Source dataset
uspto-grants-1997_01
Patent number
US05597834

Reaction notes

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