3-{3-[4-Acetyl-3-methoxy-2-(3,3,3-trifluoropropyl)-phenoxy]propoxy}-nitrobenzene → 3-{3-[4-Acetyl-3-methoxy-2-(3,3,3-trifluoropropyl)-phenoxy]propoxy}-aniline

HRID 1086927Notes

Reaction equation

HRID 1086927 reaction equation
[C:1]([C:4]1[CH:23]=[CH:22][C:7]([O:8][CH2:9][CH2:10][CH2:11][O:12][C:13]2[CH:14]=[C:15]([N+:19]([O-])=O)[CH:16]=[CH:17][CH:18]=2)=[C:6]([CH2:24][CH2:25][C:26]([F:29])([F:28])[F:27])[C:5]=1[O:30][CH3:31])(=[O:3])[CH3:2]>[Ni].O1CCCC1>[C:1]([C:4]1[CH:23]=[CH:22][C:7]([O:8][CH2:9][CH2:10][CH2:11][O:12][C:13]2[CH:14]=[C:15]([CH:16]=[CH:17][CH:18]=2)[NH2:19])=[C:6]([CH2:24][CH2:25][C:26]([F:28])([F:27])[F:29])[C:5]=1[O:30][CH3:31])(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 198186143-{3-[4-Acetyl-3-methoxy-2-(3,3,3-trifluoropropyl)-phenoxy]propoxy}-nitrobenzene

Product 1

HCID 198185853-{3-[4-Acetyl-3-methoxy-2-(3,3,3-trifluoropropyl)-phenoxy]propoxy}-aniline

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8028TetrahydrofuranSolvent

Procedure

2.0 g of Raney nickel are added to a solution of 10 g of 3-{3-[4-acetyl-3-methoxy-2-(3,3,3-trifluoropropyl)-phenoxy]-propoxy}-nitrobenzene in 100 ml of tetrahydrofuran and the starting substance is hydrogenated at room temperature. The catalyst is filtered off and washed with tetrahydrofuran. Evaporation of the filtrate under reduced pressure gives 3-{3-[4-acetyl-3-methoxy-2-(3,3,3-trifluoropropyl)-phenoxy]-propoxy}-aniline as a colourless oil.

Workup

  1. customis hydrogenated at room temperature
  2. filtrationThe catalyst is filtered off
  3. washwashed with tetrahydrofuran
  4. customEvaporation of the filtrate under reduced pressure

Sources & evidence

ORD record
ord-b30b69915aa045428b57dd91542ee757
Source dataset
uspto-grants-1991_07
Patent number
US05032606

Reaction notes

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