2-Fluoro-n-hexyl-4-nitroaniline → 2-fluoro-N1-hexylbenzene-1,4-diamine
Reaction equation
[F:1][C:2]1[CH:14]=[C:13]([N+:15]([O-])=O)[CH:12]=[CH:11][C:3]=1[NH:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]>CO.[Pd]>[F:1][C:2]1[CH:14]=[C:13]([NH2:15])[CH:12]=[CH:11][C:3]=1[NH:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
To a solution of 2-fluoro-N-hexyl-4-nitroaniline (4.37 g, 18.2 mmol) in MeOH (50 mL) was added catalyst Pd/C (0.50 g). The reaction mixture was stirred at rt under H2 overnight. The mixture was filtered, and the filtrate was concentrated in vacuo. The residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=4:1) to give the title compound as blackish oil (3.36 g, 88%).
Workup
- filtrationThe mixture was filtered
- concentrationthe filtrate was concentrated in vacuo
- customThe residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=4:1)
Sources & evidence
- ORD record
- ord-e98b622ce26d497cab4c6d38d44c1780
- Source dataset
- uspto-grants-2016_09
- Patent number
- US09434695B2
Reaction notes
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