Naproxen → Desmethylnaproxen

HRID 1882304Notes

Reaction equation

HRID 1882304 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 29 was filtered, dried (380 grams, 81%), and used as such for the next stage.

Workup

  1. temperaturewas refluxed for 10 hours
  2. additionpoured onto ice water (3000 mL)
  3. filtrationCrude 29 was filtered
  4. customdried (380 grams, 81%)

Sources & evidence

ORD record
ord-850c7d0584a34e79b1627f53cbc4b73e
Source dataset
uspto-grants-2012_11
Patent number
US08318973B2

Reaction notes

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