HCID 10012728, compound → 2-(1,2-Oxazol-5-yl)aniline

HRID 1193440Notes

Reaction equation

HRID 1193440 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[O:14][N:13]=[CH:12][CH:11]=1)([O-])=O>Cl>[NH2:1][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[O:14][N:13]=[CH:12][CH:11]=1

Participants

3

Reactant 1

HCID 10012728HCID 10012728, compound

Product 1

HCID 134898092-(1,2-Oxazol-5-yl)anilineYield 67.8%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
10 °C

Procedure

To a suspension containing 206 g of stannous chloride dihydrate in 520 ml of concentrated hydrochloric acid was cautiously added 56 g of 5-(2-nitrophenyl)isoxazole, prepared in Example 2. The resulting suspension was refluxed on a steam bath for about 1 hour, then cooled to 10° C. and filtered. The solid was added to about 600 ml of ice-water, and the suspension was made basic to a pH of about 10 with addition of 50% NaOH. The aqueous mixture was extracted with methylene chloride. After drying the methylene chloride extract over sodium sulfate, the solvent was evaporated under reduced pressure to give 32 g of the title compound as an oil.

Workup

  1. customprepared in Example 2
  2. temperatureThe resulting suspension was refluxed on a steam bath for about 1 hour
  3. filtrationfiltered
  4. additionThe solid was added to about 600 ml of ice-water
  5. additionthe suspension was made basic to a pH of about 10 with addition of 50% NaOH
  6. extractionThe aqueous mixture was extracted with methylene chloride
  7. dry with materialAfter drying the methylene chloride
  8. extractionextract over sodium sulfate
  9. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-4b46ae1b32314b3787399db12abeaf4c
Source dataset
uspto-grants-1989_03
Patent number
US04810282

Reaction notes

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