Hydrochloric Acid → HCID 66643617, compound

HRID 1695390Notes

Reaction equation

HRID 1695390 reaction equation
C[O:2][C:3]([C:5]1[N:6]([CH3:25])[N:7]=[C:8]([O:10][CH2:11][C:12]2[C:13]([C:18]3[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=3)=[N:14][O:15][C:16]=2[CH3:17])[CH:9]=1)=[O:4].[OH-].[Na+].Cl>O1CCOCC1>[F:24][C:21]1[CH:22]=[CH:23][C:18]([C:13]2[C:12]([CH2:11][O:10][C:8]3[CH:9]=[C:5]([C:3]([OH:4])=[O:2])[N:6]([CH3:25])[N:7]=3)=[C:16]([CH3:17])[O:15][N:14]=2)=[CH:19][CH:20]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 66643823HCID 66643823, compound

Product 1

HCID 66643617HCID 66643617, compoundYield 93.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 5-[3-(4-fluoro-phenyl)-5-methyl-isoxazol-4-ylmethoxy]-2-methyl-2H-pyrazole-3-carboxylic acid methyl ester (250 mg, 0.72 mmol) in dioxane (3 mL) was added aqueous sodium hydroxide (2 M, 2.0 mL, 2.0 mmol). After heating at 90° C. for 1 h the solution was cooled to room temperature and neutralized with aqueous hydrogen chloride (2 N). The resulting mixture was then extracted with ethyl acetate and water. The organic extract was then washed with water, brine, dried over sodium sulfate and evaporated to afford the title compound (222 mg, 92%) which was obtained as a white solid. MS: m/e=330.1 [M−H]−.

Workup

  1. extractionThe resulting mixture was then extracted with ethyl acetate and water
  2. extractionThe organic extract
  3. washwas then washed with water, brine
  4. dry with materialdried over sodium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-6c5dba4f1b3c4708bd9d5222ecef4495
Source dataset
uspto-grants-2012_04
Patent number
US08163728B2

Reaction notes

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