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

HRID 525965노트

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HRID 525965 반응식
[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]

참가 물질

4

반응물 3

HCID 77384-Methoxybenzyl alcoholHCID 14797Potassium HydroxideHCID 14612522HCID 14612522, 화합물

생성물 1

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

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온도
80 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-ffe41d08de304743acd4c291b74f420a
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09340556B2

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