4-Methoxybenzyl alcohol → 1-(Tert-butyl)-6,7-bis((4-methoxybenzyl)oxy)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

HRID 525965ノート

反応式

HRID 525965 の反応式
[C:1]([N:5]1[C:14]2[C:9](=[CH:10][C:11](F)=[C:12](F)[CH:13]=2)[C:8](=[O:17])[C:7]([C:18]([O:20]CC)=[O:19])=[CH:6]1)([CH3:4])([CH3:3])[CH3:2].[OH-:23].[K+].[CH3:25][O:26][C:27]1[CH:34]=[CH:33][C:30]([CH2:31][OH:32])=[CH:29][CH:28]=1>>[C:1]([N:5]1[C:14]2[C:9](=[CH:10][C:11]([O:23][CH2:31][C:30]3[CH:33]=[CH:34][C:27]([O:26][CH3:25])=[CH:28][CH:29]=3)=[C:12]([O:32][CH2:31][C:30]3[CH:33]=[CH:34][C:27]([O:26][CH3:25])=[CH:28][CH:29]=3)[CH:13]=2)[C:8](=[O:17])[C:7]([C:18]([OH:20])=[O:19])=[CH:6]1)([CH3:2])([CH3:3])[CH3:4]

参加物

4

反応物 3

HCID 77384-Methoxybenzyl alcoholHCID 14797Potassium HydroxideHCID 14612522HCID 14612522、化合物

生成物 1

HCID 867328301-(Tert-butyl)-6,7-bis((4-methoxybenzyl)oxy)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid収率 72.9%

反応条件

温度
80 °C

実験手順

A mixture of ethyl 1-(tert-butyl)-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate (50 g, 162 mmol), KOH (136 g, 2425 mmol) and 4-methoxybenzyl alcohol (201 ml, 1617 mmol) was heated at 80° C. under N2 for 8 h. LCMS showed completion of reaction. The solution was adjusted to pH 2, extracted with EA and washed with water. The organic phase was concentrated in vacuo and the crude product was triturated in Et2O to afford 1-(tert-butyl)-6,7-bis((4-methoxybenzyl)oxy)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid (61 g, 118 mmol, 72.9% yield) as pale yellow solid. LCMS: (M+H)+: 518.3.

後処理

  1. customcompletion of reaction
  2. extractionextracted with EA
  3. washwashed with water
  4. concentrationThe organic phase was concentrated in vacuo
  5. customthe crude product was triturated in Et2O

出典と根拠

ORDレコード
ord-ffe41d08de304743acd4c291b74f420a
出典データセット
uspto-grants-2016_05
特許番号
US09340556B2

反応ノート

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