Hydrochloric Acid → HCID 22170164, compound

HRID 1823291Notes

Reaction equation

HRID 1823291 reaction equation
C([O:3][C:4]([C:6]1[C:7]([C:12]2[C:17]([F:18])=[CH:16][CH:15]=[CH:14][N:13]=2)=[N:8][O:9][C:10]=1[CH3:11])=[O:5])C.[OH-].[Na+].C(O)C.Cl>O.O1CCCC1>[F:18][C:17]1[C:12]([C:7]2[C:6]([C:4]([OH:5])=[O:3])=[C:10]([CH3:11])[O:9][N:8]=2)=[N:13][CH:14]=[CH:15][CH:16]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14798Sodium HydroxideHCID 57425441HCID 57425441, compound

Product 1

HCID 22170164HCID 22170164, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Combine 3-(3-fluoro-pyridin-2-yl)-5-methyl-isoxazole-4-carboxylic acid ethyl ester (0.515 g, 0.002 mol) with aqueous sodium hydroxide (2N, 8.0 mL, 0.016 mol), ethanol (2 mL), and tetrahydrofuran (2 mL) and stir overnight at ambient temperature. Add water and adjust to approx. pH 2.0 with aqueous hydrochloric acid. Extract with ethyl acetate and dry over sodium sulfate and concentrate in vacuo. Drying nets the desired isoxazole acid (0.44 g, 97%). MS(ES): (M+1)+ 221.9, 222.9 m/z.

Workup

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

Sources & evidence

ORD record
ord-2115aa873d2d4f4bb886498497e43705
Source dataset
uspto-grants-2006_05
Patent number
US07037921B2

Reaction notes

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