2-(2-Nitrophenyl)oxazolo[5,4-b]pyridine → 2-(2-Aminophenyl)oxazolo[5,4-b]pyridine

HRID 259558Notes

Reaction equation

HRID 259558 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[O:11][C:12]2[C:17]([N:18]=1)=[CH:16][CH:15]=[CH:14][N:13]=2)([O-])=O>[Pd].C(O)C>[NH2:1][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[O:11][C:12]2[C:17]([N:18]=1)=[CH:16][CH:15]=[CH:14][N:13]=2

Participants

4

Reactant 1

HCID 124614202-(2-Nitrophenyl)oxazolo[5,4-b]pyridine

Product 1

HCID 124614212-(2-Aminophenyl)oxazolo[5,4-b]pyridine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 700 mg. of 2-(2-nitrophenyl)oxazolo[ 5,4-b]pyridine in 50 ml. of ethanol was hydrogenated over 150 mg. of 5% palladium on carbon catalyst. The catalyst was removed by filtration and the solvent was concentrated to dryness. The residue was recrystallized from chloroform-petroleum ether to give 2-(2-aminophenyl)oxazolo[ 5,4-b]pyridine, m.p. 142°-144° C.

Workup

  1. additionA mixture of 700 mg
  2. customThe catalyst was removed by filtration
  3. concentrationthe solvent was concentrated to dryness
  4. customThe residue was recrystallized from chloroform-petroleum ether

Sources & evidence

ORD record
ord-392a9a4ecd5d4a4b9e74a49444ec3132
Source dataset
uspto-grants-1977_07
Patent number
US04038396

Reaction notes

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