HCID 18354634, compound → HCID 66621373, compound

HRID 415188Notes

Reaction equation

HRID 415188 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([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:6][CH:5]=1)([O-])=O>CO.[Ni]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([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:8][CH:9]=1

Participants

4

Reactant 1

HCID 18354634HCID 18354634, compound

Product 1

HCID 66621373HCID 66621373, compoundYield 63%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

To a mixture of 2-(4-nitrophenyl)benzo[d]oxazole-4-carboxamide (800 mg, 2.83 mmol) in methanol (30 mL) was added Raney Ni (2 g), the mixture was purged into hydrogen and stirred at room temperature for 5 hr. The mixture was filtered, washed with methanol, the filtrate was evaporated under reduced pressure to obtain a solid, purified by silica gel chromatography to give 2-(4-aminophenyl)benzo[d]oxazole-4-carboxamide as a yellow solid (450 mg, yield 63%). 1H-NMR (400 MHz, DMSO-d6) δ 6.16 (s, 2H), 6.69-6.72 (d, J=9.2 Hz, 2H), 7.38-7.42 (t, J=8 Hz, 1H), 7.85-7.96 (m, 5H), 8.54 (s, 1H); LC-MS (ESI) m/z 254 [M+1]+.

Workup

  1. customthe mixture was purged into hydrogen
  2. filtrationThe mixture was filtered
  3. washwashed with methanol
  4. customthe filtrate was evaporated under reduced pressure
  5. customto obtain a solid
  6. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-b6583f67e8c640af8206776a7d3c5178
Source dataset
uspto-grants-2012_01
Patent number
US08088760B2

Reaction notes

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