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

HRID 38660Notes

Reaction equation

HRID 38660 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([C:17]2[CH2:26][C:25](=[O:27])[C:24]3[C:19](=[CH:20][C:21]4[O:30][CH2:29][O:28][C:22]=4[CH:23]=3)[N:18]=2)[CH:12]=[C:13]([O:15]C)[CH:14]=1)C1C=CC=CC=1>CO.[Pd]>[OH:15][C:13]1[CH:12]=[C:11]([C:17]2[CH2:26][C:25](=[O:27])[C:24]3[C:19](=[CH:20][C:21]4[O:30][CH2:29][O:28][C:22]=4[CH:23]=3)[N:18]=2)[CH:10]=[C:9]([O:8][CH3:1])[CH:14]=1

Participants

4

Reactant 1

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

Product 1

HCID 666595082-(3-Hydroxy-5-methoxyphenyl)-6,7-methylenedioxyquinolin-4-oneYield 77%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A suspension of 0.5 g (1.245 mmol) of 165 and 0.25 g of palladium (10 wt % on activated carbon) in 60 mL of methanol was stirred at room temperature under hydrogen gas atmosphere for 24 h. The precipitate were collected and dissolved in 10% NaOH solution and then filtered. The filtrate was acidified with dil aq HCl and the precipitate was then collected and washed with acetone and water to give 166.

Workup

  1. customThe precipitate were collected
  2. dissolutiondissolved in 10% NaOH solution
  3. filtrationfiltered
  4. customthe precipitate was then collected
  5. washwashed with acetone and water

Sources & evidence

ORD record
ord-b3283e0473644294a2c1891d17746257
Source dataset
uspto-grants-2013_09
Patent number
US08524740B2

Reaction notes

Loading…