N-(2-fluoro-5-nitrophenyl)-3,4,5,6-tetrahydrophthalimide → N-(2-fluoro-5-aminophenyl)-3,4,5,6-tetrahydrophthalimide

HRID 1655837Notes

Reaction equation

HRID 1655837 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-])=O)=[CH:4][C:3]=1[N:11]1[C:20](=[O:21])[C:15]2[CH2:16][CH2:17][CH2:18][CH2:19][C:14]=2[C:12]1=[O:13].[H][H]>[Ni].COCCOC.C(O)C>[NH2:8][C:5]1[CH:6]=[CH:7][C:2]([F:1])=[C:3]([N:11]2[C:12](=[O:13])[C:14]3[CH2:19][CH2:18][CH2:17][CH2:16][C:15]=3[C:20]2=[O:21])[CH:4]=1

Participants

5

Reactant 2

HCID 13560456N-(2-fluoro-5-nitrophenyl)-3,4,5,6-tetrahydrophthalimideHCID 178418361HCID 178418361, compound

Product 1

HCID 10332826N-(2-fluoro-5-aminophenyl)-3,4,5,6-tetrahydrophthalimideYield 94.9%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 20074477Dimethoxyethane ethanolSolvent

Procedure

Wet Raney Nickel (0.9 g) is added to a solution of N-(2-fluoro-5-nitrophenyl)-1-cyclohexene-1,2-dicarboximide (1.0 g, 3.4 mmol) in a 4:1 ethylene glycol dimethyl ether/ethanol solution. The reaction mixture is hydrogenated over 45 psi of hydrogen until the reaction mixture takes up 9 psi. The reaction mixture is filtered through diatomaceous earth and concentrated in vacuo to obtain a yellow residue. Chromatography of the residue gives the title product as a yellow-orange solid (0.84 g, mp 134°-136° C.) which is identified by 1H and 13C NMR spectral analyses.

Workup

  1. filtrationThe reaction mixture is filtered through diatomaceous earth
  2. concentrationconcentrated in vacuo
  3. customto obtain a yellow residue

Sources & evidence

ORD record
ord-a1aee1ecb5544c139cec30e6661fcfff
Source dataset
uspto-grants-1993_10
Patent number
US05252536

Reaction notes

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