Naproxen → Desmethylnaproxen

HRID 2405171Notes

Reaction equation

HRID 2405171 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-927e46c5dc214a78a9a0d61e88802c62
Source dataset
uspto-grants-2014_08
Patent number
US08802892B2

Reaction notes

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