Lithium Hydroxide → 3-Aminoisoxazole-5-carboxylic acid

HRID 1891410Notes

Reaction equation

HRID 1891410 reaction equation
[NH2:1][C:2]1[CH:6]=[C:5]([C:7]([O:9]CC)=[O:8])[O:4][N:3]=1.[OH-].[Li+]>C(#N)C.O>[NH2:1][C:2]1[CH:6]=[C:5]([C:7]([OH:9])=[O:8])[O:4][N:3]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 11126498Ethyl 3-aminoisoxazole-5-carboxylate

Product 1

HCID 552646873-Aminoisoxazole-5-carboxylic acidYield 90.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To a solution of ethyl 3-aminoisoxazole-5-carboxylate (prepared according to Lepage, Francis; Hublot, Bernard; Adolphe, Pierre Sylvie. Preparation of alkyl 3-aminoisoxazole-5-carboxylates. Fr. Demande (1998), FR 2750425) (0.790 g, 5.06 mmol) in acetonitrile (28 mL) and water (9.5 mL) was added lithium hydroxide (0.550 g, 23.0 mmol). The resulting mixture was stirred at rt for 3 h. The reaction was quenched with 1 N HCl. Organic solvent was removed in vacuo. The resulting precipitate was filtered and dried to give the product as white solid (585 mg, 90%). LCMS calculated for C4H5N2O3 (M+H)+: m/z=129.0.

Workup

  1. customThe reaction was quenched with 1 N HCl
  2. customOrganic solvent was removed in vacuo
  3. filtrationThe resulting precipitate was filtered
  4. customdried

Sources & evidence

ORD record
ord-906661068fda4ef5844c1bf1a44881ff
Source dataset
uspto-grants-2013_08
Patent number
US08507541B2

Reaction notes

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