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

HRID 1763094Notes

Reaction equation

HRID 1763094 reaction equation
[Cl:1][C:2]1[C:8]([O:9][CH2:10][C:11]#[CH:12])=[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][CH2:10][C:11]#[CH: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 13272927Benzenamine, 4-chloro-2-fluoro-5-(2-propynyloxy)-

Product 1

HCID 1079551H-Isoindole-1,3(2H)-dione, 2-(4-chloro-2-fluoro-5-(2-propynyloxy)phenyl)-4,5,6,7-tetrahydro-Yield 40.9%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

4-Chloro-2-fluoro-5-(2-propynyloxy)aniline (1.9 g) and 3,4,5,6-tetrahydrophthalic anhydride (1.52 g) were dissolved in acetic acid (20 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 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 1.3 g of N-[4-chloro-2-fluoro-5-(2-propynyloxy)phenyl]3,4,5,6-tetrahydrophthalimide (Compound No. 3). M.P. 136.4° C.

Workup

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

Sources & evidence

ORD record
ord-674fb034644c41a285f322c0a24cc3ec
Source dataset
uspto-grants-1989_05
Patent number
US04835324

Reaction notes

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