Methyl 2-(quinolin-2-yl)acetate → 2-Quinolineacetic acid, 1,2,3,4-tetrahydro-, methyl ester

HRID 2081499노트

반응식

HRID 2081499 반응식
[N:1]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]=[CH:8][C:2]=1[CH2:3][C:4]([O:6][CH3:7])=[O:5].[H][H]>C(O)C.[Pt]=O>[NH:1]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH2:9][CH2:8][CH:2]1[CH2:3][C:4]([O:6][CH3:7])=[O:5]

참가 물질

5

반응물 2

HCID 10608140Methyl 2-(quinolin-2-yl)acetateHCID 178418361HCID 178418361, 화합물

생성물 1

HCID 103529122-Quinolineacetic acid, 1,2,3,4-tetrahydro-, methyl ester수율 111.1%

시약·촉매·용매 2

HCID 82844Platinum oxide (PtO)촉매HCID 702Ethanol용매

실험 절차

In 120 ml of ethanol, 6 g of methyl quinaldinate was reduced by hydrogen in the presence of 400 mg of platinum oxide to give 6.8 g of methyl 1,2,3,4-tetrahydroquinaldinate as an oil. 3.0 g of the resulting methylester was further reduced in a dry ether by 1 g of lithium aluminum hydride to give 2.6 g of 1,2,3,4-tetrahydro-2-quinolinemethanol. A mixture of 1.6 g of the resulting alcohol, 0.93 ml of dimethylsulfonic acid, 2.16 g of calcium carbonate and 8 ml of water was stirred at room temperature for 6 hours. To the reaction mixture was added ether and insolubles were removed by filtration. The organic portion was separated, washed with water and dried over anhydrous sodium sulfate. After removal of the solvent under reduced pressure, the organic portion was purified by silica gel column chromatography (eluent: chloroform) to give 1.4 g of 1-methyl-1,2,3,4-tetrahydro-2-quinolinemethanol as a pale yellow oil.

출처 및 근거

ORD 기록
ord-536cff425f404baaaacfca60e19dc4fe
출처 데이터셋
uspto-grants-1993_02
특허 번호
US05183811

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