Sodium Hydroxide → HCID 178486764, compound

HRID 81976Notes

Reaction equation

HRID 81976 reaction equation
[CH3:1][C:2]1[C:6]([C:7]2[CH:16]=[C:15]3[C:10]([C:11]([OH:22])=[C:12]([C:17]([O:19]CC)=[O:18])[CH:13]=[N:14]3)=[CH:9][C:8]=2[O:23][CH3:24])=[C:5]([CH3:25])[O:4][N:3]=1.[OH-].[Na+]>C(O)C>[CH3:1][C:2]1[C:6]([C:7]2[CH:16]=[C:15]3[C:10]([C:11]([OH:22])=[C:12]([C:17]([OH:19])=[O:18])[CH:13]=[N:14]3)=[CH:9][C:8]=2[O:23][CH3:24])=[C:5]([CH3:25])[O:4][N:3]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 178469491Ethyl 7-(3,5-dimethyl-4-isoxazolyl)-4-hydroxy-6-(methyloxy)-3-quinolinecarboxylate

Product 1

HCID 178486764HCID 178486764, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl 7-(3,5-dimethyl-4-isoxazolyl)-4-hydroxy-6-(methyloxy)-3-quinolinecarboxylate (for a preparation see Intermediate 4) (28.4 g, 83 mmol) was suspended in a mixture of ethanol (200 ml) and NaOH (2M, 124 ml, 249 mmol) and the mixture was heated at reflux overnight, then evaporated to around 100 ml volume and the resulting solution washed with MTBE (100 ml). The aqueous layer was acidified to pH4 with 1M HCl, then the resulting solid collected by filtration and washed with water and dried overnight at 40° C. in the vacuum oven to give 7-(3,5-dimethyl-4-isoxazolyl)-4-hydroxy-6-(methyloxy)-3-quinolinecarboxylic acid (24.5 g, 78 mmol, 94% yield) as pale yellow solid. LCMS Rt 0.76 min, MH+ 315

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux overnight
  3. customevaporated to around 100 ml volume
  4. washthe resulting solution washed with MTBE (100 ml)
  5. filtrationthe resulting solid collected by filtration
  6. washwashed with water
  7. customdried overnight at 40° C. in the vacuum oven

Sources & evidence

ORD record
ord-0da3cb864d8349f99344b7fd009ef7c7
Source dataset
uspto-grants-2014_09
Patent number
US08846709B2

Reaction notes

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