2-fluoro-4-nitro-N,N-bis(2-propoxyethyl)aniline → 2-fluoro-N1,N1-bis(2-propoxyethyl)benzene-1,4-diamine

HRID 56175Notes

Reaction equation

HRID 56175 reaction equation
[F:1][C:2]1[CH:20]=[C:19]([N+:21]([O-])=O)[CH:18]=[CH:17][C:3]=1[N:4]([CH2:11][CH2:12][O:13][CH2:14][CH2:15][CH3:16])[CH2:5][CH2:6][O:7][CH2:8][CH2:9][CH3:10]>CO.[Pd]>[F:1][C:2]1[CH:20]=[C:19]([NH2:21])[CH:18]=[CH:17][C:3]=1[N:4]([CH2:11][CH2:12][O:13][CH2:14][CH2:15][CH3:16])[CH2:5][CH2:6][O:7][CH2:8][CH2:9][CH3:10]

Participants

4

Reactant 1

HCID 1179660542-fluoro-4-nitro-N,N-bis(2-propoxyethyl)aniline

Product 1

HCID 1179660932-fluoro-N1,N1-bis(2-propoxyethyl)benzene-1,4-diamineYield 37.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 2-fluoro-4-nitro-N,N-bis(2-propoxyethyl)aniline (1.47 g, 4.48 mmol) in MeOH (50 mL) was added catalyst Pd/C (0.15 g). The reaction was stirred at rt under H2 overnight, then filtered. 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 (0.50 g, 34%).

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated in vacuo
  3. customThe residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=4:1)

Sources & evidence

ORD record
ord-25c91682f2944550be8439c63d4c550c
Source dataset
uspto-grants-2016_09
Patent number
US09434695B2

Reaction notes

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