Naproxen → Desmethylnaproxen

HRID 386926Notes

Reaction equation

HRID 386926 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 grams, 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 36 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 36 was filtered
  4. customdried (380 grams, 81%)

Sources & evidence

ORD record
ord-30ca927dffff42d7a685dc8e9c32649b
Source dataset
uspto-grants-2013_02
Patent number
US08372882B2

Reaction notes

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