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

HRID 1388549Notes

Reaction equation

HRID 1388549 reaction equation
[Cl:1][C:2]1[C:8]([O:9][CH:10]([CH3:12])[CH3:11])=[CH:7][C:5]([NH2:6])=[C:4]([F:13])[CH:3]=1.[C:14]1(=O)[O:19][C:17](=[O:18])[C:16]2[CH2:20][CH2:21][CH2:22][CH2:23][C:15]1=2.O>C(O)(=O)C>[Cl:1][C:2]1[C:8]([O:9][CH:10]([CH3:11])[CH3:12])=[CH:7][C:5]([N:6]2[C:17](=[O:18])[C:16]3[CH2:20][CH2:21][CH2:22][CH2:23][C:15]=3[C:14]2=[O:19])=[C:4]([F:13])[CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 124753,4,5,6-Tetrahydrophthalic anhydrideHCID 158649Benzenamine, 4-chloro-2-fluoro-5-(1-methylethoxy)-

Product 1

HCID 1586501H-Isoindole-1,3(2H)-dione, 2-(4-chloro-2-fluoro-5-(1-methylethoxy)phenyl)-4,5,6,7-tetrahydro-Yield 46.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

4-Chloro-2-fluoro-5-isopropoxyaniline (1.3 g) and 3,4,5,6-tetrahydrophthalic anhydride (1.12 g) were dissolved in acetic acid (10 ml) and refluxed for 3 hours. The resultant mixture was allowed to cool to room temperature and poured into water, followed by extraction with ether. The ether extract was washed with water, dried over anhydrous sodium sulfate and subjected to filtration. The filtrate was concentrated under reduced pressure and the residue was purified by silica gel chromatography to obtain 1.0 g of N-(4-chloro-2-fluoro-5-isopropoxyphenyl)-3,4,5,6-tetrahydrophthalimide (Compound No. 1). M.P., 81°-82° C.

Workup

  1. temperaturerefluxed for 3 hours
  2. extractionfollowed by extraction with ether
  3. extractionThe ether extract
  4. washwas washed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationsubjected to filtration
  7. concentrationThe filtrate was concentrated under reduced pressure
  8. customthe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-bf802eb3d0194646ab412a9180516d0c
Source dataset
uspto-grants-1984_02
Patent number
US04431822

Reaction notes

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