HCID 66914929, compound → 2-Fluoro-4-oxazol-2-ylaniline

HRID 880514Notes

Reaction equation

HRID 880514 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:11]2[O:12][CH:13]=[CH:14][N:15]=2)[CH:5]=[CH:6][C:7]=1[N+:8]([O-])=O>CO.O>[F:1][C:2]1[CH:3]=[C:4]([C:11]2[O:12][CH:13]=[CH:14][N:15]=2)[CH:5]=[CH:6][C:7]=1[NH2:8]

Participants

4

Reactant 1

HCID 66914929HCID 66914929, compound

Product 1

HCID 669151462-Fluoro-4-oxazol-2-ylanilineYield 83%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A stirred solution of 2-(3-fluoro-4-nitro-phenyl)oxazole (500 mg, 2.40 mmol) in methanol (10 mL) was added to stannous chloride (2.7 g, 12.01 mmol) under nitrogen atmosphere and stirred for 16 h. The reaction mixture was diluted with water and filtered through Celite. The filtrate was basified with bicarbonate solution and extracted with ethyl acetate. The organic layer was washed with water, brine, dried over anhydrous sodium sulfate and concentrated in vacuo to afford 2-fluoro-4-oxazol-2-yl aniline (350 mg, 83%) as a yellow colour solid.

Workup

  1. filtrationfiltered through Celite
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water, brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-91f718a3b31c45b38ac60cd787a2c484
Source dataset
uspto-grants-2015_03
Patent number
US08993574B2

Reaction notes

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