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

HRID 525965Notes

Reaction equation

HRID 525965 reaction equation
[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]

Participants

4

Reactant 3

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

Product 1

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

Conditions

Temperature
80 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-ffe41d08de304743acd4c291b74f420a
Source dataset
uspto-grants-2016_05
Patent number
US09340556B2

Reaction notes

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