Chloroform → N-(3-amino-4-chloro-6-fluorophenyl)-3,4,5,6-tetrahydrophthalimide

HRID 1761323Notes

Reaction equation

HRID 1761323 reaction equation
[Cl:1][C:2]1[C:7]([N+:8]([O-])=O)=[CH:6][C:5]([N:11]2[C:15](=[O:16])[C:14]3[CH2:17][CH2:18][CH2:19][CH2:20][C:13]=3[C:12]2=[O:21])=[C:4]([F:22])[CH:3]=1.C(Cl)(Cl)Cl>C(O)(=O)C.[Fe]>[NH2:8][C:7]1[CH:6]=[C:5]([N:11]2[C:15](=[O:16])[C:14]3[CH2:17][CH2:18][CH2:19][CH2:20][C:13]=3[C:12]2=[O:21])[C:4]([F:22])=[CH:3][C:2]=1[Cl:1]

Participants

5

Reactant 2

HCID 6212ChloroformHCID 15590179N-(4-chloro-2-fluoro-5-nitrophenyl)-3,4,5,6-tetrahydrophthalimide

Product 1

HCID 15590180N-(3-amino-4-chloro-6-fluorophenyl)-3,4,5,6-tetrahydrophthalimideYield 51%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent2×

Procedure

A solution of N-(4-chloro-2-fluoro-5-nitrophenyl)-3,4,5,6-tetrahydrophthalimide (16.2 g) in acetic acid (200 ml) is dropwise added to a suspension of iron powder (14 g) in a 5% aqueous acetic acid (30 ml) at 90°-100° C. and refluxed for 1 hour. After being allowed to cool, chloroform is added to the resultant mixture, followed by filtration. The organic layer is separated from the filtrate, washed with a saturated sodium hydrogen carbonate solution, dried and concentrated. The residue is recrystallized from a mixture of ether and petroleum ether to give 7.5 g of N-(3-amino-4-chloro-6-fluorophenyl)-3,4,5,6-tetrahydrophthalimide. M.P., 144.5°-146.5° C.

Workup

  1. temperaturerefluxed for 1 hour
  2. temperatureto cool
  3. filtrationfollowed by filtration
  4. customThe organic layer is separated from the filtrate
  5. washwashed with a saturated sodium hydrogen carbonate solution
  6. customdried
  7. concentrationconcentrated
  8. customThe residue is recrystallized from a mixture of ether and petroleum ether

Sources & evidence

ORD record
ord-3cb8eec69ecc4e82b264f5ba25e8057a
Source dataset
uspto-grants-1989_05
Patent number
US04826533

Reaction notes

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