Sodium Hydroxide → 2-(3-Benzyloxy-5-methoxyphenyl)-6,7-methylenedioxyquinolin-4-one

HRID 38659Notes

Reaction equation

HRID 38659 reaction equation
[C:1]([C:4]1[C:5]([NH:13][C:14](=O)[C:15]2[CH:20]=[C:19]([O:21][CH3:22])[CH:18]=[C:17]([O:23][CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH:16]=2)=[CH:6][C:7]2[O:11][CH2:10][O:9][C:8]=2[CH:12]=1)(=[O:3])[CH3:2].[OH-].[Na+]>O1CCOCC1>[CH2:24]([O:23][C:17]1[CH:16]=[C:15]([C:14]2[CH2:2][C:1](=[O:3])[C:4]3[C:5](=[CH:6][C:7]4[O:11][CH2:10][O:9][C:8]=4[CH:12]=3)[N:13]=2)[CH:20]=[C:19]([O:21][CH3:22])[CH:18]=1)[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 58052627N-(6-acetylbenzo[d][1,3]-dioxol-5-yl)-3-(benzyloxy)-5-methoxybenzamide

Product 1

HCID 666594662-(3-Benzyloxy-5-methoxyphenyl)-6,7-methylenedioxyquinolin-4-one

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Into a suspension of 164 (3.33 g, 0.0079 mmol) in 200 mL of 1,4-dioxane was added sodium hydroxide (2.50 g, 0.0635 mmol). The mixture was refluxed for 24 h. After the reaction mixture was evaporated, 100 mL of 10% ammonium chloride solution was added. The mixture was stirred for 12 h, and then the precipitate was collected and washed with water and acetone.

Workup

  1. temperatureThe mixture was refluxed for 24 h
  2. customAfter the reaction mixture was evaporated
  3. addition100 mL of 10% ammonium chloride solution was added
  4. customthe precipitate was collected
  5. washwashed with water and acetone

Sources & evidence

ORD record
ord-1b486e1d8f394a25a00b5ff4ff704e9e
Source dataset
uspto-grants-2013_09
Patent number
US08524740B2

Reaction notes

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