HCID 3089143, compound → 2-(4-Amino-phenyl)-benzooxazol-5-ylamine

HRID 325086Notes

Reaction equation

HRID 325086 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[O:11][C:12]3[CH:18]=[CH:17][C:16]([N+:19]([O-])=O)=[CH:15][C:13]=3[N:14]=2)=[CH:6][CH:5]=1)([O-])=O>O1CCOCC1.[Pd]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([C:10]2[O:11][C:12]3[CH:18]=[CH:17][C:16]([NH2:19])=[CH:15][C:13]=3[N:14]=2)=[CH:8][CH:9]=1

Participants

4

Reactant 1

HCID 3089143HCID 3089143, compound

Product 1

HCID 6143852-(4-Amino-phenyl)-benzooxazol-5-ylamine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
53 °C

Procedure

A 7.5-gram portion of the 2-(p-nitrophenyl)-5-nitrobenzoxazole is dissolved in 100 milliliters of 1,4-dioxane. A 10% palladium-on-carbon catalyst (2.0 grams) is added, and the mixture stirred under nitrogen. The mixture is heated to 53° C., and hydrogen gas is bubbled into the mixture for about 6.5 hours. The catalyst is then filtered off and the remaining solution added to water. The solvent and water are then evaporated off to yield 2-(p-aminophenyl)-5-aminobenzoxazole.

Workup

  1. customhydrogen gas is bubbled into the mixture for about 6.5 hours
  2. filtrationThe catalyst is then filtered off
  3. additionthe remaining solution added to water
  4. customThe solvent and water are then evaporated off

Sources & evidence

ORD record
ord-3f51ccde83e146e988cdf257cfdb0311
Source dataset
uspto-grants-2001_04
Patent number
US06222044B1

Reaction notes

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