Hydrochloric Acid → HCID 22170131, compound

HRID 1823279Notes

Reaction equation

HRID 1823279 reaction equation
C([O:3][C:4]([C:6]1[C:7]([C:12]2[CH:13]=[N:14][CH:15]=[CH:16][C:17]=2[Cl:18])=[N:8][O:9][C:10]=1[CH3:11])=[O:5])C.[OH-].[Na+].C(O)C.Cl>O1CCCC1>[Cl:18][C:17]1[CH:16]=[CH:15][N:14]=[CH:13][C:12]=1[C:7]1[C:6]([C:4]([OH:5])=[O:3])=[C:10]([CH3:11])[O:9][N:8]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14798Sodium HydroxideHCID 574254393-(4-Chloro-pyridin-3-yl)-5-methyl-isoxazole-4-carboxylic acid ethyl ester

Product 1

HCID 22170131HCID 22170131, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Combine 3-(4-chloro-pyridin-3-yl)-5-methyl-isoxazole-4-carboxylic acid ethyl ester (0.90 g, 0.003 mol) with aqueous sodium hydroxide (2N, 7.0 mL, 0.014 mol), ethanol (2 mL), and tetrahydrofuran (2 mL) and stir overnight at ambient temperature. Adjust the aqueous mixture to approx. pH 2.5 with aqueous hydrochloric acid. Extract with ethyl acetate and dry the combined extracts over sodium sulfate and concentrate in vacuo. Drying nets the desired isoxazole acid as a light solid (0.78 g, 97%). MS(ES): (M+1)+ 239.0, 241.0 m/z.

Workup

  1. extractionExtract with ethyl acetate
  2. dry with materialdry the combined extracts over sodium sulfate
  3. concentrationconcentrate in vacuo
  4. customDrying

Sources & evidence

ORD record
ord-d8ed08fa0aeb4f4586e1f0ff9706dcec
Source dataset
uspto-grants-2006_05
Patent number
US07037921B2

Reaction notes

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