Water → 5-(Furan-2-yl)isoxazol-3-amine

HRID 606281Notes

Reaction equation

HRID 606281 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[O:10][N:9]=[C:8](C(O)=O)[CH:7]=1.C1C=CC(P([N:28]=[N+]=[N-])(C2C=CC=CC=2)=O)=CC=1.O>C1C=CC=CC=1>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[O:10][N:9]=[C:8]([NH2:28])[CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 199401P,P-Diphenylphosphinic azideHCID 10909825-(2-Furyl)isoxazole-3-carboxylic acid

Product 1

HCID 132302595-(Furan-2-yl)isoxazol-3-amineYield 40%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a solution of 2.0 g of 5-furan-2-yl-isoxazole-3-carboxylic acid and 6.2 mL of TEA in benzene was added 3.61 mL of DPPA at room temperature. After refluxing for 1.5 hrs, 30 mL of distilled water was added and then the resulting solution was refluxed for an additional 30 min. The reaction solution was concentrated under reduced pressure, and the concentrate was purified by column chromatography on silica gel to obtain 0.6 g of 5-furan-2-yl-isoxazol-3-ylamine (Yield: 40%).

Workup

  1. temperatureAfter refluxing for 1.5 hrs
  2. temperaturethe resulting solution was refluxed for an additional 30 min
  3. concentrationThe reaction solution was concentrated under reduced pressure
  4. customthe concentrate was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-4ebb5004b63c4d4eaca013a6f286976e
Source dataset
uspto-grants-2011_03
Patent number
US07915297B2

Reaction notes

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