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

HRID 1088563ノート

反応式

HRID 1088563 の反応式
[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]

参加物

5

反応物 2

HCID 10608140Methyl 2-(quinolin-2-yl)acetateHCID 178418361HCID 178418361、化合物

生成物 1

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

試薬・触媒・溶媒 2

HCID 82844Platinum oxide (PtO)触媒HCID 702Ethanol溶媒

実験手順

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.

出典と根拠

ORDレコード
ord-a015c6c485554d669fb3ad8d4db6acd5
出典データセット
uspto-grants-1990_10
特許番号
US04962096

反応ノート

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