Nabumetone → Nabumetone 2,3-naphthalenediol

HRID 271035

Reaction equation

HRID 271035 reaction equation
[CH3:1][C:2]([CH2:4][CH2:5][C:6]1[CH:7]=[CH:8][C:9]2[CH:10]=[C:11]([O:16][CH3:17])[CH:12]=[CH:13][C:14]=2[CH:15]=1)=[O:3].[CH:18]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:21]=[C:20]([OH:28])[C:19]=1[OH:29]>[N+](C)([O-])=O>[CH:21]1[C:22]2[C:27](=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:18]=[C:19]([OH:29])[C:20]=1[OH:28].[CH3:1][C:2]([CH2:4][CH2:5][C:6]1[CH:7]=[CH:8][C:9]2[CH:10]=[C:11]([O:16][CH3:17])[CH:12]=[CH:13][C:14]=2[CH:15]=1)=[O:3].[CH:13]1[C:14]2[C:9](=[CH:8][CH:7]=[CH:6][CH:15]=2)[CH:10]=[C:11]([OH:16])[C:12]=1[OH:28]

Participants

5

Reactant 2

HCID 4409Nabumetone2×HCID 70912,3-Dihydroxynaphthalene

Product 2

HCID 70912,3-DihydroxynaphthaleneHCID 67107975Nabumetone 2,3-naphthalenediolYield 68%

Reagents, catalysts & solvents 1

HCID 6375NitromethaneSolvent

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.

Workup

  1. temperaturewith heating
  2. customA solid was formed as the solution
  3. temperaturecooled
  4. filtrationThe solid was filtered from the remaining solvent
  5. customdried in the air

Sources & evidence

ORD record
ord-f4aa8ea5a5884b2695c8e9085aab7d64
Source dataset
uspto-grants-2008_11
Patent number
US07452555B2

Linked notes

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