1H-Isoindole-1,3(2H)-dione, 2-(4-chloro-2-fluoro-5-(1-methylethoxy)phenyl)-4,5,6,7-tetrahydro- → N-(2-fluoro-4 chloro-5-isopropoxyphenyl)hexahydrophthalimide

HRID 867348Notes

Reaction equation

HRID 867348 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([O:9][CH:10]([CH3:12])[CH3:11])=[CH:4][C:3]=1[N:13]1[C:17](=[O:18])[C:16]2[CH2:19][CH2:20][CH2:21][CH2:22][C:15]=2[C:14]1=[O:23]>[Pt].C(Cl)Cl>[F:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([O:9][CH:10]([CH3:12])[CH3:11])=[CH:4][C:3]=1[N:13]1[C:17](=[O:18])[CH:16]2[CH2:19][CH2:20][CH2:21][CH2:22][CH:15]2[C:14]1=[O:23]

Participants

4

Reactant 1

HCID 1586501H-Isoindole-1,3(2H)-dione, 2-(4-chloro-2-fluoro-5-(1-methylethoxy)phenyl)-4,5,6,7-tetrahydro-

Product 1

HCID 15591734N-(2-fluoro-4 chloro-5-isopropoxyphenyl)hexahydrophthalimideYield 100%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 6344DichloromethaneSolvent

Procedure

A pressure bottle was charged with 1.01 g (0.003 mol) of N-(2 fluoro- 4-chloro-5-isopropoxyphenyl) -3,4,5,6-tetrahydrophthalimide (see U.S. Pat. No. 4,431,822 for the preparation of this compound), 0.10 g of 5% Pt/C, and 60 ml of methylene chloride, placed on a Paar apparatus, and hydrogenated at 40 psi for 3 hours. Thin layer chromatography showed that the hydrogenation of the double bond was complete. The reaction mixture was filtered through Celite, and solvent removed from the filtrate to give 1.0 g (100% yield) of N-(2-fluoro-4 chloro-5-isopropoxyphenyl)hexahydrophthalimide as a white solid.

Workup

  1. filtrationThe reaction mixture was filtered through Celite, and solvent
  2. customremoved from the filtrate

Sources & evidence

ORD record
ord-80db33950e2347ab98cd4bac47ef7dca
Source dataset
uspto-grants-1988_10
Patent number
USH0000531

Reaction notes

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