HCID 89524851, compound → HCID 89524847, compound

HRID 920277Notes

Reaction equation

HRID 920277 reaction equation
[N+:1]([C:4]1[CH:21]=[CH:20][C:7]2[N:8]([CH:12]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH3:13])[C:9](=[O:11])[O:10][C:6]=2[CH:5]=1)([O-])=O>CCO.[Pd]>[NH2:1][C:4]1[CH:21]=[CH:20][C:7]2[N:8]([CH:12]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH3:13])[C:9](=[O:11])[O:10][C:6]=2[CH:5]=1

Participants

4

Reactant 1

HCID 89524851HCID 89524851, compound

Product 1

HCID 89524847HCID 89524847, compoundYield 62.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Into a solution of 6-nitro-3-(1-phenylethyl)benzo[d]oxazol-2(3H)-one (40-2, 7.89 g, 27.8 mmol) in EtOH (139 ml) was added Pd/C (295 mg, 2.78 mmol). The reaction was stirred under 1 atm of H2 for 2 h, filtered through celite, concentrated and purified using a 50 g SCX column (eluting with 2 N NH3 in MeOH) to yield 6-amino-3-(1-phenylethyl)benzo[d]oxazol-2(3H)-one (4.4 g, 17.3 mmol). LRMS C15H14N202 [M+H] calc 255.1, obs 255.4.

Workup

  1. filtrationfiltered through celite,
  2. concentrationconcentrated
  3. custompurified
  4. washa 50 g SCX column (eluting with 2 N NH3 in MeOH)

Sources & evidence

ORD record
ord-395a2f3c3e9442dd9e35ef22cbd47bca
Source dataset
uspto-grants-2016_03
Patent number
US09273040B2

Reaction notes

Loading…