Tetrahydrofuran → 5,6,7,8-Tetrahydro-8-(3,4-dimethylbenzoyl)quinoline
Reaction equation
[N:1]1[C:10]2[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.C([Li])CCC.[CH3:16][C:17]1[CH:18]=[C:19]([CH:22]=[CH:23][C:24]=1[CH3:25])[C:20]#N.C1C[O:29]CC1>>[CH3:16][C:17]1[CH:18]=[C:19]([CH:22]=[CH:23][C:24]=1[CH3:25])[C:20]([CH:9]1[C:10]2[N:1]=[CH:2][CH:3]=[CH:4][C:5]=2[CH2:6][CH2:7][CH2:8]1)=[O:29]Participants
Conditions
- Temperature
- 0 °C
Procedure
5,6,7,8-Tetrahydroquinoline (7.2g 0.054M) was dissolved in THF (50ml) and cooled to 0° C. 35ml of a solution of n-butyl lithium (1.6M in hexane) was added. The mixture was left for 20 minutes then a solution of 3,4,-dimethyl-benzonitrile (7g 0.053M) in THF (50ml) was added. The mixture was allowed to stand for 30 minutes them 2MHCl (100ml) was added. The mixture was allowed to stand for 16 hours after which the resulting yellow crystals were filtered off and washed with isopropyl alcohol then ether to give 6.17g of the title compound as the hydrochloride. The mother liquids were diluted with 2M HCl and extracted with hexane. A small quantity of solid was obtained filtered off and washed . with isopropyl alcohol then ether to give a further 2.2g of the title compound hydrochloride dihydrate m.p. 236°-7° C.
Workup
- waitto stand for 30 minutes
- additionthem 2MHCl (100ml) was added
- waitto stand for 16 hours
- filtrationafter which the resulting yellow crystals were filtered off
- washwashed with isopropyl alcohol
Sources & evidence
- ORD record
- ord-c237c6ab71134724a1fbb9199a48f4ee
- Source dataset
- uspto-grants-1991_03
- Patent number
- US05001131
Reaction notes
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