Methanol → 3-Pyridin-2-yl-isoxazole-4-carboxylic acid

HRID 1923504Notes

Reaction equation

HRID 1923504 reaction equation
C([O:3][C:4]([C:6]1[C:7]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=2)=[N:8][O:9][CH:10]=1)=[O:5])C.O.[OH-].[Li+].CO>C1COCC1.O>[N:12]1[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=1[C:7]1[C:6]([C:4]([OH:5])=[O:3])=[CH:10][O:9][N:8]=1

Participants

6

Reactant 3

HCID 887MethanolHCID 168937Lithium hydroxide, monohydrateHCID 666437583-Pyridin-2-yl-isoxazole-4-carboxylic acid ethyl ester

Product 1

HCID 666435283-Pyridin-2-yl-isoxazole-4-carboxylic acidYield 79%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 3-pyridin-2-yl-isoxazole-4-carboxylic acid ethyl ester (9.52 g, 44 mmol) in THF (530 mL) was added a solution of lithium hydroxide monohydrate (11.0 g, 263 mmol) in water (265 mL) followed by methanol (265 mL) at 0° C. and the resulting mixture stirred at room temperature for 1 h. The mixture was then evaporated to half volume and then acidified to pH 4 with HCl (1N) and cooled to 0° C. for 30 min. A solid precipitated and was filtered off and dried to afford the title compound (6.55 g, 79%) which was obtained as an off white solid. MS: m/e=189.3 [M−H]−.

Workup

  1. customThe mixture was then evaporated to half volume
  2. temperaturecooled to 0° C. for 30 min
  3. customA solid precipitated
  4. filtrationwas filtered off
  5. customdried

Sources & evidence

ORD record
ord-8ebdf8955a7f41c99d33f77f672d0cb3
Source dataset
uspto-grants-2012_05
Patent number
US08178522B2

Reaction notes

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