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

HRID 1284615Notes

Reaction equation

HRID 1284615 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]>C(O)(=O)C.[Fe]>[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

4

Reactant 1

HCID 13560456N-(2-fluoro-5-nitrophenyl)-3,4,5,6-tetrahydrophthalimide

Product 1

HCID 10332826N-(2-fluoro-5-aminophenyl)-3,4,5,6-tetrahydrophthalimideYield 78.1%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent2×

Procedure

To a suspension of electrolytic iron powders (9 g) in 5% acetic acid (200 g) under reflux, a solution of N-(2-fluoro-5-nitrophenyl)-3,4,5,6-tetrahydrophthalimide (VII) (15 g) in acetic acid (50 g) was added dropwise. After completion of the addition, the resultant mixture was heated under reflux for 30 minutes, cooled and filtered. The filtrate was diluted with water and extracted with ethyl acetate. The extract was concentrated, and the precipitated crystals were collected by filtration to give 10.5 g of N-(2-fluoro-5-aminophenyl)-3,4,5,6-tetrahydrophthalimide (VIII). M.P., 117°-119° C.

Workup

  1. temperatureunder reflux
  2. additionAfter completion of the addition
  3. temperatureunder reflux for 30 minutes
  4. temperaturecooled
  5. filtrationfiltered
  6. additionThe filtrate was diluted with water
  7. extractionextracted with ethyl acetate
  8. concentrationThe extract was concentrated
  9. filtrationthe precipitated crystals were collected by filtration

Sources & evidence

ORD record
ord-f2428b245c6b404c88ec25b51f2a3b19
Source dataset
uspto-grants-1986_01
Patent number
US04563535

Reaction notes

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