Sodium Hydroxide → HCID 178486764, compound

HRID 1042994Notes

Reaction equation

HRID 1042994 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, compound

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 58, 70.2 g, 205 mmol,) was suspended in a mixture of ethanol (200 ml) and sodium hydroxide (2M, 308 ml, 615 mmol) and the mixture was heated at reflux overnight. The reaction was concentrated to ca 200 ml in vacuo, diluted with water (500 ml) and the resulting solution washed with ethyl acetate (200 ml). The aqueous phase was acidified to pH4 with hydrochloric acid (1M), the resulting suspension stirred vigorously for 10 min. The solid was collected by filtration, washed with water (200 ml) and dried overnight at 40° C. in vacuo to give 7-(3,5-dimethyl-4-isoxazolyl)-4-hydroxy-6-(methyloxy)-3-quinolinecarboxylic acid as a beige solid (54.7 g). Used without further purification.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux overnight
  3. concentrationThe reaction was concentrated to ca 200 ml in vacuo
  4. additiondiluted with water (500 ml)
  5. washthe resulting solution washed with ethyl acetate (200 ml)
  6. filtrationThe solid was collected by filtration
  7. washwashed with water (200 ml)
  8. customdried overnight at 40° C. in vacuo

Sources & evidence

ORD record
ord-aaa8f10cbe8f43318fd74199f619d3c1
Source dataset
uspto-grants-2013_10
Patent number
US08557984B2

Reaction notes

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