HCID 4137682, compound → 5-benzoxazolamine, 2-(3-aminophenyl)-

HRID 325088Notes

Reaction equation

HRID 325088 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([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:7]=[CH:8][CH:9]=1)([O-])=O>C(O)CC.[Pd]>[NH2:1][C:4]1[CH:5]=[C:6]([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:7]=[CH:8][CH:9]=1

Participants

4

Reactant 1

HCID 4137682HCID 4137682, compound

Product 1

HCID 7625455-benzoxazolamine, 2-(3-aminophenyl)-

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 10311-PropanolSolvent

Conditions

Temperature
70 °C

Procedure

A 11.1-gram portion of the 2-(m-nitrophenyl)-5-nitrobenzoxazole is dissolved in 200 milliliters of n-propanol. A 10% palladium-on-carbon catalyst (2.0 grams) is added, and the mixture stirred under nitrogen. The mixture is heated to 70° C., and hydrogen gas is bubbled into the mixture until substantially all the nitro groups have been reduced to primary amine groups, as indicated by liquid chromatography. The catalyst is then filtered off and the remaining solution added to water. The solvent and water are then evaporated off to yield 2-(m-aminophenyl)-5-aminobenzoxazole.

Workup

  1. customhydrogen gas is bubbled into the mixture until substantially all the nitro groups
  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-769ea3da9059411597f6f74131294edb
Source dataset
uspto-grants-2001_04
Patent number
US06222044B1

Reaction notes

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