2-(3-Nitrophenyl)oxazolo[4,5-b]pyridine → 3-(Oxazolo[4,5-b]pyridin-2-yl)aniline

HRID 259540Notes

Reaction equation

HRID 259540 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:10]2[O:11][C:12]3[C:13]([N:18]=2)=[N:14][CH:15]=[CH:16][CH:17]=3)[CH:7]=[CH:8][CH:9]=1)([O-])=O>[Pd].C(O)C>[NH2:1][C:4]1[CH:5]=[C:6]([C:10]2[O:11][C:12]3[C:13]([N:18]=2)=[N:14][CH:15]=[CH:16][CH:17]=3)[CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 1

HCID 124613742-(3-Nitrophenyl)oxazolo[4,5-b]pyridine

Product 1

HCID 6110863-(Oxazolo[4,5-b]pyridin-2-yl)aniline

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 700mg. of 2-(3-nitrophenyl)oxazolo[4,5-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 chloroformpetroleum ether to give 2-(3-aminophenyl)oxazolo[4,5-b]pyridine, m.p. 179°-180.5° C.

Workup

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

Sources & evidence

ORD record
ord-fc2a510ad2b148efac1e78dda0e36836
Source dataset
uspto-grants-1977_07
Patent number
US04038396

Reaction notes

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