Hydrochloric Acid → 5,6,7,8-Tetrahydro-4-methyl-8-(3,4-dimethylbenzoyl)quinoline hydrochloride

HRID 359457ノート

反応式

HRID 359457 の反応式
[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.[CH3:12][C:13]1[CH:14]=NC2C(=O)CCC[C:21]=2[CH:22]=1.[ClH:24].[CH2:25]1[CH2:29][O:28][CH2:27][CH2:26]1>>[ClH:24].[CH3:1][C:2]1[C:11]2[CH2:10][CH2:9][CH2:8][CH:7]([C:27](=[O:28])[C:26]3[CH:25]=[CH:29][C:22]([CH3:21])=[C:13]([CH3:14])[CH:12]=3)[C:6]=2[N:5]=[CH:4][CH:3]=1

参加物

5

反応物 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 1856675,6,7,8-Tetrahydro-4-methylquinolineHCID 123582233-Methyl-6,7-dihydroquinolin-8(5H)-one

生成物 1

HCID 200649765,6,7,8-Tetrahydro-4-methyl-8-(3,4-dimethylbenzoyl)quinoline hydrochloride

実験手順

After 0.5h, a 1.36M solution of butyl lithium (11.2ml, 0.017m) was added at 0.° C. and the mixture stirred at this temperature for a further 0.5h. A solution of 3,4-dimethylbenzonitrile (2.6g, 0.02m) in THF (20ml) was added rapidly and after 0.5h a solution of 2M hydrochloric acid (40ml) was added and the aqueous phase separated. This was basified with solid potassium carbonate and the mixture extracted with ether. The mixture was purified by chromatography on silica using ether as eluant. The isolated product was dissolved in ether and acidified with ethereal HCl to give 5,6,7,8-tetrahydro-4-methyl-8-(3,4-dimethylbenzoyl)quinoline hydrochloride (2.5g, 53%) m.p. 237°-9° C. (Found; C,72.25; H, 7.0;N, 4.4 C19H21NO.HCl requires C, 71.8; H, 7.1; N, 4.3%).

後処理

  1. customthe aqueous phase separated
  2. extractionthe mixture extracted with ether
  3. customThe mixture was purified by chromatography on silica
  4. dissolutionThe isolated product was dissolved in ether

出典と根拠

ORDレコード
ord-9383fa4093ef4d2e861a8c2886bf6567
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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