Reaction #358217

ord-f4aa8ea5a5884b2695c8e9085aab7d64

Reaction equation

COc1ccc2cc(CCC(C)=O)ccc2c1
nabumetone
Oc1cc2ccccc2cc1O
2,3-naphthalenediol
COc1ccc2cc(CCC(C)=O)ccc2c1
nabumetone
→
Oc1cc2ccccc2cc1O
2,3-naphthalenediol
COc1ccc2cc(CCC(C)=O)ccc2c1.Oc1cc2ccccc2cc1O
nabumetone 2,3-naphthalenediol
Yield 68.0%

Reactants

COc1ccc2cc(CCC(C)=O)ccc2c1
nabumetone
Oc1cc2ccccc2cc1O
2,3-naphthalenediol
COc1ccc2cc(CCC(C)=O)ccc2c1
nabumetone

Reagents

None

Solvents

C[N+](=O)[O-]
nitromethane

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Temperaturewith heating
  2. 2
    OtherA solid was formed as the solution
  3. 3
    Temperaturecooled
  4. 4
    FiltrationThe solid was filtered from the remaining solvent
  5. 5
    Otherdried in the air

Procedure

As a demonstrative example, a cocrystal comprising a neutral API is described in this example. Cocrystals of nabumetone (a neutral API) and 2,3-naphthalenediol were prepared as follows. A 4.01 g sample of 2,3-naphthalenediol and 5.7 g of nabumetone were dissolved in 50 mL of nitromethane with heating. A solid was formed as the solution cooled and was allowed to stand overnight. The solid was filtered from the remaining solvent and dried in the air to yield 6.61 g (68%) of nabumetone:2,3-naphthalenediol (1:1) cocrystal.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07452555B2uspto-grants-2008_11