2,2,4-Trimethyl-1,2-dihydroquinoline → Quinoline, 1,2,3,4-tetrahydro-2,2,4-trimethyl-

HRID 1088436노트

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HRID 1088436 반응식
[CH3:1][C:2]1([CH3:13])[CH:11]=[C:10]([CH3:12])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[NH:3]1.[H][H]>C(O)C.[Pd]>[CH3:1][C:2]1([CH3:13])[CH2:11][CH:10]([CH3:12])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[NH:3]1

참가 물질

5

반응물 2

HCID 89812,2,4-Trimethyl-1,2-dihydroquinolineHCID 178418361HCID 178418361, 화합물

생성물 1

HCID 107292Quinoline, 1,2,3,4-tetrahydro-2,2,4-trimethyl-수율 89%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 702Ethanol용매

실험 절차

In 10 ml of ethanol was dissolved 2.0 g (11.5 millimoles) of 1,2-dihydro-2,2,4-trimethylquinoline, and 0.4 g of 10% Pd-C was added to the solution and reaction was carried out at 60° C. in a hydrogen atmosphere for 7 hours. The catalyst was removed by filtration and the filtrate was concentrated under reduced pressure to obtain 1.8 g (the yield was 89%) of 2,2,4-trimethyl-1,2,3,4-tetrahydroquinoline in the form of a light-brown oil. To 0.5 g (3.7 millimoles) of 4-hydroxymethylimidazole hydrochloride was added 3 ml of thionyl chloride and reaction was carried out at 50° C. for 2 hours. The excess of thionyl chloride was removed by distillation under reduced pressure. The residue was dissolved in 10 ml of DMF and a solution of 1.1 g (6.3 millimoles) of 2,2,4-trimethyl-1,2,3,4-tetrahydroquinoline in 5 ml of DMF was added to the above solution at 100° C. Reaction was carried out for 1 hour. DMF was removed from the reaction mixture by distillation under reduced pressure. An aqueous solution of sodium hydrogen-carbonate was added to the residue and the mixture was extracted with dichloromethane. The organic layer was dried with anhydrous sodium sulfate and concentrated under reduced pressure to obtain a light-green oil. The oil was purified by the silica gel column chromatography (developing solvent; ethyl acetate) to obtain 0.35 g (the yield was 39%) of 4-[1-(2,2,4-trimethyl-1,2,3,4-tetrahydroquinolyl)methyl]imidazole in the form of a colorless crystal. Reaction was carried out in the same manner as described in Example 3 by using 4-[1-(2,2,4-trimethyl-1,2,3,4-tetrahydroquinolyl)methyl]imidazole to obtain 0.35 g (the yield was 30%) of intended compound No. 8 in the form of a light-brown oil.

후처리

  1. additionwas added to the solution and reaction
  2. customThe catalyst was removed by filtration
  3. concentrationthe filtrate was concentrated under reduced pressure

출처 및 근거

ORD 기록
ord-21fe455cc5ec41988c49f9750026778b
출처 데이터셋
uspto-grants-1990_10
특허 번호
US04962200

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