HCID 23132493, compound → HCID 23132476, compound

HRID 2102804Notes

Reaction equation

HRID 2102804 reaction equation
[N+:1]([C:4]1[CH:21]=[CH:20][C:7]2[N:8]=[C:9]([NH:11][C:12](=[O:19])[C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[O:10][C:6]=2[CH:5]=1)([O-])=O.[H][H]>CN(C)C=O.[Pd]>[NH2:1][C:4]1[CH:21]=[CH:20][C:7]2[N:8]=[C:9]([NH:11][C:12](=[O:19])[C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[O:10][C:6]=2[CH:5]=1

Participants

5

Reactant 2

HCID 23132493HCID 23132493, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 23132476HCID 23132476, compoundYield 45.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of N-(6-nitrobenzoxazol-2-yl)benzamide (2.03 g, 7.17 mmol) in dimethylformamide (60 mL), palladium on charcoal (1.52 g, 10% Pd, 1.43 mmol Pd) was added and the air was replaced with hydrogen (1 bar). The mixture was stirred for 2 h at 60° C. and then overnight at r.t. The palladium was removed by filtration through a pad of celite. After concentration to 20 mL, water was added and the resulting precipitate was separated by filtration to obtain N-(6-aminobenzoxazol-2-yl)benzamide (0.823 g, 3.25 mmol, 45%) as a brown solid. LC/ESI-MS: m/z=254 [M+H]+; m/z=252 [M−H]−; Rt=1.92 min.

Workup

  1. customovernight
  2. customat r.t
  3. customThe palladium was removed by filtration through a pad of celite
  4. concentrationAfter concentration to 20 mL, water
  5. additionwas added
  6. customthe resulting precipitate was separated by filtration

Sources & evidence

ORD record
ord-18d33567c1494058b82a32ea0e9925c6
Source dataset
uspto-grants-2009_08
Patent number
US07576090B2

Reaction notes

Loading…