Hydrochloric Acid → 5-(4-Cyanophenyl)-3-isoxazolecarboxylic acid

HRID 1424527Notes

Reaction equation

HRID 1424527 reaction equation
C([O:3][C:4]([C:6]1[CH:10]=[C:9]([C:11]2[CH:16]=[CH:15][C:14]([C:17]#[N:18])=[CH:13][CH:12]=2)[O:8][N:7]=1)=[O:5])C.[OH-].[Na+].Cl>O1CCCC1>[C:17]([C:14]1[CH:13]=[CH:12][C:11]([C:9]2[O:8][N:7]=[C:6]([C:4]([OH:5])=[O:3])[CH:10]=2)=[CH:16][CH:15]=1)#[N:18]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 56930123HCID 56930123, compound

Product 1

HCID 681584235-(4-Cyanophenyl)-3-isoxazolecarboxylic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 5-(4-cyano-phenyl)-isoxazole-3-carboxylic acid ethyl ester (100 mg) and 1 N aqueous NaOH solution (1.24 mL) in tetrahydrofuran (4.5 mL) is stirred at room temperature for 3 h. The reaction mixture is acidified with 3 N hydrochloric acid and concentrated in vacuo. The residue is triturated with water; the precipitate is filtered off and dried to give the title compound. LC (method 3): tR=1.01 min; Mass spectrum (ESI+): m/z=215 [M+H]+.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue is triturated with water
  3. filtrationthe precipitate is filtered off
  4. customdried

Sources & evidence

ORD record
ord-437bbb2f0c794daaa6fe84471fe30348
Source dataset
uspto-grants-2015_01
Patent number
US08927726B2

Reaction notes

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