Hydrochloric Acid → HCID 22170145, compound

HRID 1823299Notes

Reaction equation

HRID 1823299 reaction equation
C([O:3][C:4]([C:6]1[C:7]([C:12]2[C:17]([Cl:18])=[CH:16][C:15]([Cl:19])=[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>[Cl: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]=[C:15]([Cl:19])[CH:16]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14798Sodium HydroxideHCID 69652716HCID 69652716, compound

Product 1

HCID 22170145HCID 22170145, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Combine 3-(3,5-dichloro-pyridin-2-yl)-5-methyl-isoxazole-4-carboxylic acid ethyl ester (0.755 g, 0.0025 mol) with aqueous sodium hydroxide (2N, 6.0 mL, 0.012 mol), ethanol (2 mL), and tetrahydrofuran (2 mL) and stir overnight at ambient temperature. Add water and adjusted to approx. pH 3.0 with aqueous hydrochloric acid. Extract with ethyl acetate and dry over sodium sulfate and concentrate in vacuo. Drying nets the desired isoxazole acid as a tan solid(0.65 g, 95%). MS (ES): (M+1)+ 273.0,275.0 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-be57234384974f18a6d441ec5726b233
Source dataset
uspto-grants-2006_05
Patent number
US07037921B2

Reaction notes

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