Hydroxyamine hydrochloride → HCID 58542033, compound

HRID 1966795Notes

Reaction equation

HRID 1966795 reaction equation
[CH3:1][O:2][C:3](=[O:17])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10](=[O:16])/[CH:11]=[CH:12]/[N:13](C)C.Cl.NO>CO>[CH3:1][O:2][C:3](=[O:17])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[O:16][N:13]=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 58542024HCID 58542024, compound

Product 1

HCID 58542033HCID 58542033, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2-((E)-3-dimethylamino-acryloyl)-benzoic acid methyl ester (1.295 mg, 5.552 mmol) in methanol (21 mL) is added hydroxylamine hydrochloride (964.5 mg, 13.88 mmol). The reaction mixture is heated to reflux for 1.5 hours. After this time, the reaction mixture is loaded onto silica gel and purified using silica gel flash column chromatography with 1-10% MeOH in CH2Cl2 as the eluent to give 2-isoxazol-5-yl-benzoic acid methyl ester (587 mg, 52%).

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureto reflux for 1.5 hours
  3. custompurified

Sources & evidence

ORD record
ord-67272fc344b34d87b4826b052e58371c
Source dataset
uspto-grants-2013_04
Patent number
US08420655B2

Reaction notes

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