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

HRID 1284614Notes

Reaction equation

HRID 1284614 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:15](=[O:16])[C:14]2[CH2:17][CH2:18][CH2:19][CH2:20][C:13]=2[C:12]1=[O:21].[H][H]>C(OCC)(=O)C.[Pt](=O)=O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[CH:4][C:3]=1[N:11]1[C:15](=[O:16])[C:14]2[CH2:17][CH2:18][CH2:19][CH2:20][C:13]=2[C:12]1=[O:21]

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 99.9%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 8857Ethyl AcetateSolvent

Procedure

N-(2-Fluoro-5-nitrophenyl)-3,4,5,6-tetrahydrophthalimide (VII) (5 g) and platinum dioxide (0.2 g) were suspended in ethyl acetate (50 ml), and the resultant suspension was allowed to catalytic reduction at room temperature under atmospheric pressure until 1.3 liters of hydrogen was taken up. The reaction mixture was filtered and concentrated to give 4.48 g of N-(2-fluoro-5-aminophenyl)-3,4,5,6-tetrahydrophthalimide (VIII). M.P., 117°-119° C.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-0c17a0014699455f8837b7b272c8928a
Source dataset
uspto-grants-1986_01
Patent number
US04563535

Reaction notes

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