Tetrahydrofuran → 5,6,7,8-Tetrahydro-8-(3,4-dimethylbenzoyl)quinoline

HRID 359462ノート

反応式

HRID 359462 の反応式
[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]

参加物

5

反応物 4

HCID 8028Tetrahydrofuran2 回HCID 663355,6,7,8-TetrahydroquinolineHCID 898843,4-DimethylbenzonitrileHCID 178418339Butyllithium

生成物 1

HCID 146209815,6,7,8-Tetrahydro-8-(3,4-dimethylbenzoyl)quinoline

反応条件

温度
0 °C

実験手順

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.

後処理

  1. waitto stand for 30 minutes
  2. additionthem 2MHCl (100ml) was added
  3. waitto stand for 16 hours
  4. filtrationafter which the resulting yellow crystals were filtered off
  5. washwashed with isopropyl alcohol

出典と根拠

ORDレコード
ord-c237c6ab71134724a1fbb9199a48f4ee
出典データセット
uspto-grants-1991_03
特許番号
US05001131

反応ノート

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