Hydrochloric Acid → 3-(3-Cyano-phenyl)-isoxazole-5-carboxylic acid

HRID 1062655Notes

Reaction equation

HRID 1062655 reaction equation
C([C:5]1[C:6]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([C:16]#[N:17])[CH:11]=2)=[N:7][O:8][CH:9]=1)(OC)=O.[OH2:18].[OH-:19].[Li+].Cl.[CH3:22]O>O>[C:16]([C:12]1[CH:11]=[C:10]([C:6]2[CH:5]=[C:9]([C:22]([OH:19])=[O:18])[O:8][N:7]=2)[CH:15]=[CH:14][CH:13]=1)#[N:17]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 168937Lithium hydroxide, monohydrateHCID 22282436HCID 22282436, compound

Product 1

HCID 222824483-(3-Cyano-phenyl)-isoxazole-5-carboxylic acidYield 43%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 0.90 g (3.9 mmol) of 4-carbomethoxy-3-(3-cyanophenyl)isoxazole, 0.25 g (6.0 mmol) of lithium hydroxide monohydrate in 1 mL water and 2 mL methanol is stirred under N2 for 5 hours. The reaction mixture was acidified to pH 3 with 1N HCl, extracted with 10 mL EtOAc three times, dried with MgSO4 and concentrated in vacuo to give 0.36 g (43%) of the desired acid. 1H NMR (CDCl3) δ: 8.94 (s, 1H); 8.01 (s, 1H); 7.94 (d, 1H); 7.60 (d, 2H); 7.43 (t, 1H).

Workup

  1. extractionextracted with 10 mL EtOAc three times
  2. dry with materialdried with MgSO4
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-69ee1f2a869f4d2ab3116ef5b28e7fec
Source dataset
uspto-grants-2005_11
Patent number
US06962935B2

Reaction notes

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