[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 1360776Notes

Reaction equation

HRID 1360776 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-289a245b27b948e2890f223a63444d17
Source dataset
uspto-grants-2011_02
Patent number
US07879850B2

Reaction notes

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