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

HRID 359457노트

반응식

HRID 359457 반응식
[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

참가 물질

5

반응물 4

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

생성물 1

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

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-9383fa4093ef4d2e861a8c2886bf6567
출처 데이터셋
uspto-grants-1991_03
특허 번호
US05001131

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