4-(5-(4-Methoxyphenyl)-1,3,4-oxadiazol-2-yl)-2-nitroaniline → 4-[5-(4-Methoxy-phenyl)-[1,3,4]oxadiazol-2-yl]-benzene-1,2-diamine

HRID 1360767Notes

Reaction equation

HRID 1360767 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[O:13][C:12]([C:14]3[CH:19]=[CH:18][C:17]([NH2:20])=[C:16]([N+:21]([O-])=O)[CH:15]=3)=[N:11][N:10]=2)=[CH:5][CH:4]=1>CCO.C1COCC1.O=[Pt]=O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[O:13][C:12]([C:14]3[CH:15]=[C:16]([NH2:21])[C:17]([NH2:20])=[CH:18][CH:19]=3)=[N:11][N:10]=2)=[CH:7][CH:8]=1

Participants

4

Reactant 1

HCID 669667784-(5-(4-Methoxyphenyl)-1,3,4-oxadiazol-2-yl)-2-nitroaniline

Product 1

HCID 669663924-[5-(4-Methoxy-phenyl)-[1,3,4]oxadiazol-2-yl]-benzene-1,2-diamine

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

A solution of 4-[5-(4-methoxyphenyl)-[1,3,4]oxadiazol-2-yl]-2-nitrophenylamine (1.0 g, 3.21 mmol) in 80 mL of EtOH/THF (1:1) was hydrogenated over PtO2 (100 mg) at one atm for 2-4 h. The catalyst was filtered through Celite and washed with EtOH and THF. The solvent was removed under reduced pressure to give the title compound as a yellow solid. MS: m/z 283 (M+1).

Workup

  1. filtrationThe catalyst was filtered through Celite
  2. washwashed with EtOH and THF
  3. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-091d031039294f53ae9f3d4504e4a83b
Source dataset
uspto-grants-2011_02
Patent number
US07879850B2

Reaction notes

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