Sodium Hydroxide → 3-[2-(5-Methyl-3-phenyl-4-isoxazolyl)ethynyl]benzoic acid

HRID 1984643Notes

Reaction equation

C[O:2][C:3](=[O:24])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]#[C: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:5]=1.[OH-].[Na+]>C(O)C>[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[C:11]#[C:10][C:6]1[CH:5]=[C:4]([CH:9]=[CH:8][CH:7]=1)[C:3]([OH:24])=[O:2]

Participants

Conditions

Temperature: 80 °C

Procedure

3-(5-Methyl-3-phenyl-isoxazol-4-ylethynyl)-benzoic acid methyl ester (600 mg, 1.89 mmol) was treated with ethanol (12 mL) and aqueous sodium hydroxide (1 M, 7.56 mL, 7.56 mmol). The reaction mixture was heated for 1.5 h at 80° C. After concentration and dilution with water (9 mL) the pH was adjusted to 1.5 by adding hydrochloric acid (1 M, 8 mL). The resulting suspension was stirred for 30 min at 0° C. and filtered. Washing with ice-cold water (10 mL) and drying afforded the title compound (546 mg, 95%) as a light brown solid. MS: m/e=304.1 [M+H]+.

Workup

concentrationAfter concentration and dilution with water (9 mL) the pH
additionby adding hydrochloric acid (1 M, 8 mL)
filtrationfiltered
washWashing with ice-cold water (10 mL)
customdrying

Sources & evidence

ORD record: ord-aaf70020ddf64c08a2f4e22155df1217
Source dataset: uspto-grants-2009_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07544704B2

Reaction notes

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