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

HRID 359457Notes

Reaction equation

HRID 359457 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.[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

Participants

5

Reactant 4

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

Product 1

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

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-9383fa4093ef4d2e861a8c2886bf6567
Source dataset
uspto-grants-1991_03
Patent number
US05001131

Reaction notes

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