Naproxen → Desmethylnaproxen

HRID 2169692Notes

Reaction equation

HRID 2169692 reaction equation
[CH3:1][C@H:2]([C:15]([OH:17])=[O:16])[C:3]1[CH:4]=[CH:5][C:6]2[CH:7]=[C:8]([O:13]C)[CH:9]=[CH:10][C:11]=2[CH:12]=1>Br>[OH:13][C:8]1[CH:7]=[C:6]2[C:11](=[CH:10][CH:9]=1)[CH:12]=[C:3]([CH:2]([CH3:1])[C:15]([OH:17])=[O:16])[CH:4]=[CH:5]2

Participants

3

Reactant 1

HCID 156391Naproxen

Product 1

HCID 162920Desmethylnaproxen

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Procedure

A mixture of Naproxen (500 g, 2.774 mmol) and 48% HBr (1500 ml) was refluxed for 10 hours, poured onto ice water (3000 ml) and stirred for 30 minutes. Crude 5 was filtered, dried (380 grams, 81%) and used as such for next stage.

Workup

  1. temperaturewas refluxed for 10 hours
  2. additionpoured onto ice water (3000 ml)
  3. filtrationCrude 5 was filtered
  4. customdried (380 grams, 81%)

Sources & evidence

ORD record
ord-12540e1904624b809b9bf3bb11c00d78
Source dataset
uspto-grants-2015_06
Patent number
USRE045548E1

Reaction notes

Loading…