Hydrochloric Acid → 3-(5-Methyl-3-phenyl-isoxazol-4-ylmethoxy)-isoxazole-5-carboxylic acid

HRID 1920903Notes

Reaction equation

HRID 1920903 reaction equation
C[O:2][C:3]([C:5]1[O:9][N:8]=[C:7]([O:10][CH2:11][C:12]2[C:13]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[N:14][O:15][C:16]=2[CH3:17])[CH:6]=1)=[O:4].[OH-].[Na+].Cl>O1CCOCC1>[CH3:17][C:16]1[O:15][N:14]=[C:13]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:12]=1[CH2:11][O:10][C:7]1[CH:6]=[C:5]([C:3]([OH:4])=[O:2])[O:9][N:8]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 674922963-(5-Methyl-3-phenyl-isoxazol-4-ylmethoxy)-isoxazole-5-carboxylic acid methyl ester

Product 1

HCID 674920693-(5-Methyl-3-phenyl-isoxazol-4-ylmethoxy)-isoxazole-5-carboxylic acidYield 94.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 3-(5-methyl-3-phenyl-isoxazol-4-ylmethoxy)-isoxazole-5-carboxylic acid methyl ester (209 mg, 0.66 mmol) in dioxane (5 mL) was added aqueous sodium hydroxide (2 N, 2 mL). After heating at reflux for 1 h the mixture was cooled to room temperature and acidified with HCl (4 N, 2 mL). Purification by filtration and drying afforded the title compound (187 mg, 94%) which was obtained as a white solid. MS: m/e=299.1 [M−H]−.

Workup

  1. temperatureAfter heating
  2. temperatureat reflux for 1 h the mixture
  3. customPurification
  4. filtrationby filtration
  5. customdrying

Sources & evidence

ORD record
ord-0b771a432a774ab39bf20994e0d6739b
Source dataset
uspto-grants-2012_05
Patent number
US08173652B2

Reaction notes

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