[5-(4-Amino-3-nitrophenyl)-[1,3,4]oxadiazol-2-yl]-(3-chlorophenyl)-amine → 4-[5-(3-Chlorophenylamino)-[1,3,4]oxadiazol-2-yl]-benzene-1,2-diamine

HRID 1513272Notes

Reaction equation

HRID 1513272 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:12][C:11]([NH:13][C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([Cl:20])[CH:15]=3)=[N:10][N:9]=2)=[CH:4][C:3]=1[N+:21]([O-])=O>CO.O=[Pt]=O>[Cl:20][C:16]1[CH:15]=[C:14]([NH:13][C:11]2[O:12][C:8]([C:5]3[CH:4]=[C:3]([NH2:21])[C:2]([NH2:1])=[CH:7][CH:6]=3)=[N:9][N:10]=2)[CH:19]=[CH:18][CH:17]=1

Participants

4

Reactant 1

HCID 66966422[5-(4-Amino-3-nitrophenyl)-[1,3,4]oxadiazol-2-yl]-(3-chlorophenyl)-amine

Product 1

HCID 669663754-[5-(3-Chlorophenylamino)-[1,3,4]oxadiazol-2-yl]-benzene-1,2-diamine

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 887MethanolSolvent

Procedure

A suspension of [5-(4-amino-3-nitrophenyl)-[1,3,4]oxadiazol-2-yl]-(3-chlorophenyl)-amine (245 mg, 0.74 mmol) and PtO2 (50 mg) in MeOH (30 mL) was hydrogenated at one atm for 4 h. The catalyst was filtered over Celite and the filtrate was evaporated under reduced pressure to give the title compound. This was used directly in the next reaction.

Workup

  1. filtrationThe catalyst was filtered over Celite
  2. customthe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-26ac8c49fe894fddb7a8b8e4750028c0
Source dataset
uspto-grants-2012_07
Patent number
US08217065B2

Reaction notes

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