HCID 66621468, compound → HCID 66621296, compound

HRID 415182Notes

Reaction equation

HRID 415182 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:10]2[O:11][C:12]3[C:13](=[C:15]([C:19]([NH2:21])=[O:20])[CH:16]=[CH:17][CH:18]=3)[N:14]=2)[CH:7]=[CH:8][CH:9]=1)([O-])=O>CO.[Ni]>[NH2:1][C:4]1[CH:5]=[C:6]([C:10]2[O:11][C:12]3[C:13](=[C:15]([C:19]([NH2:21])=[O:20])[CH:16]=[CH:17][CH:18]=3)[N:14]=2)[CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 1

HCID 66621468HCID 66621468, compound

Product 1

HCID 66621296HCID 66621296, compoundYield 42.4%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

To a mixture of 2-(3-nitrophenyl)benzo[d]oxazole-4-carboxamide (700 mg, 2.47 mmol) in methanol (30 mL) was added Raney Ni (2 g). The mixture was purged with hydrogen and stirred at room temperature for 5 hr. Then the mixture was filtered and washed with methanol; the filtrate was evaporated under reduced pressure and purified by silica gel chromatography to obtain 2-(3-aminophenyl)benzo[d]oxazole-4-carboxamide as a yellow solid (265 mg, yield 42%). 1H-NMR (400 MHz, DMSO-d6) δ 5.57 (s, 2H), 6.83-6.86 (dd, J1=8 Hz, J2=2 Hz, 1H), 7.25-7.29 (t, J=8 Hz, 1H), 7.42-7.44 (d, J=8 Hz, 1H), 7.51-7.56 (m, 2H), 7.96-8.00 (t, J=8 Hz, 2H), 8.07 (s, 1H), 8.47 (s, 1H); LC-MS (ESI) m/z 254 [M+1]+.

Workup

  1. customThe mixture was purged with hydrogen
  2. filtrationThen the mixture was filtered
  3. washwashed with methanol
  4. customthe filtrate was evaporated under reduced pressure
  5. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-dc911b92c4e44b949d0da7dc2db3382a
Source dataset
uspto-grants-2012_01
Patent number
US08088760B2

Reaction notes

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