4-(Benzo[d]oxazol-2-yl)-2-nitrobenzenamine → 4-(Benzo[d]oxazol-2-yl)benzene-1,2-diamine

HRID 252844Notes

Reaction equation

HRID 252844 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[CH:15]=[CH:14][C:13]([NH2:16])=[C:12]([N+:17]([O-])=O)[CH:11]=1>CO.[Pd]>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[CH:11]=[C:12]([NH2:17])[C:13]([NH2:16])=[CH:14][CH:15]=1

Participants

4

Reactant 1

HCID 146378894-(Benzo[d]oxazol-2-yl)-2-nitrobenzenamine

Product 1

HCID 146378974-(Benzo[d]oxazol-2-yl)benzene-1,2-diamineYield 87.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a stirred solution of 226 (517 mg, 1.77 mmol) in methanol (20 mL) was added palladium on charcoal (10%, 188 mg). The reaction was stirred under hydrogen atmosphere for 18 hours, filtered through a celite pad; the filtrate was evaporated under reduced pressure to afford title compound 227 (350 mg, 87% yield). 1H NMR: (DMSO) δ 7.673-7.641 (m, 2H), 7.39 (d, J=2.0 Hz, 1H), 7.32-7.30 (m, 3H), 6.64 (d, J=8.0 Hz, 1H). MS: (calc.) 225.2; (obt.) 226.1 (MH)+.

Workup

  1. filtrationfiltered through a celite pad
  2. customthe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-383f5a88bdf3457da5022b0c12101a31
Source dataset
uspto-grants-2011_01
Patent number
US07868205B2

Reaction notes

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