3-chloro-4-{4-[3-(1H-imidazol-1-yl)propyl]phenoxy}nitrobenzene → 3-chloro-4-{4-[3-(1H-imidazol-1-yl)propyl]phenoxy}aniline

HRID 1787083Notes

Reaction equation

HRID 1787083 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N+:23]([O-])=O)[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][CH2:17][N:18]2[CH:22]=[CH:21][N:20]=[CH:19]2)=[CH:11][CH:10]=1>CO.[Pt]>[Cl:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][C:7]=1[O:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:15][CH2:16][CH2:17][N:18]2[CH:22]=[CH:21][N:20]=[CH:19]2)=[CH:13][CH:14]=1)[NH2:23]

Participants

4

Reactant 1

HCID 675213043-chloro-4-{4-[3-(1H-imidazol-1-yl)propyl]phenoxy}nitrobenzene

Product 1

HCID 675211543-chloro-4-{4-[3-(1H-imidazol-1-yl)propyl]phenoxy}anilineYield 45.2%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 3-chloro-4-{4-[3-(1H-imidazol-1-yl)propyl]phenoxy}nitrobenzene (669 mg) in methanol (7 mL) was added 5% Pt/C (140 mg), and the mixture was stirred under hydrogen atmosphere at room temperature for 16 hrs. 5% Pt/C was filtered off and the filtrate was concentrated. The residue was purified by basic silica gel column chromatography (eluent, ethyl acetate:hexane=80:20→100:0) and further washed with diethyl ether and hexane to give the title compound (277 mg) as a powder.

Workup

  1. filtration5% Pt/C was filtered off
  2. concentrationthe filtrate was concentrated
  3. customThe residue was purified by basic silica gel column chromatography (eluent, ethyl acetate:hexane=80:20→100:0)
  4. washfurther washed with diethyl ether and hexane

Sources & evidence

ORD record
ord-9f3ea9e203b14268bbef232e96c7413e
Source dataset
uspto-grants-2009_03
Patent number
US07507740B2

Reaction notes

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