Phthalic Anhydride → HCID 2755705, compound

HRID 1770494Notes

Reaction equation

HRID 1770494 reaction equation
S([N:11]1[CH:15]=[C:14]([NH2:16])[CH:13]=[N:12]1)(C1C=CC(C)=CC=1)(=O)=O.[C:17]1(=[O:27])[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:19](=[O:26])O1>CN(C=O)C.C(#N)C.O>[NH:11]1[CH:15]=[C:14]([N:16]2[C:19](=[O:26])[C:20]3[C:25](=[CH:24][CH:23]=[CH:22][CH:21]=3)[C:17]2=[O:27])[CH:13]=[N:12]1

Participants

5

Reactant 2

HCID 6811Phthalic AnhydrideHCID 57944975HCID 57944975, compound

Product 1

HCID 2755705HCID 2755705, compoundYield 92.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21891449acetonitrile N,N-dimethylformamideSolvent

Procedure

1-tosyl-1H-pyrazol-4-amine (example 9-1b) (3 g, 12.7 mmol) and isobenzofuran-1,3-dione (1.9 g, 13 mmol) were stirred in DMF/Acetonitrile (1/1) (20 mL) at 100° C. for 1 hour. The mixture was cooled and diluted with H2O. The precipitate was collected by filtration, washed with additional water followed by ethyl acetate and hexanes. The solid product was dried under high vacuum to afford 2-(1H-pyrazol-4-yl) isoindoline-1,3-dione (2.5 g, 92%) as a yellow solid. MS M+H calculated 214.1. Found 214.1. 1H NMR (CDCl3, 400 MHz) δ 7.93-8.10 (m, 6H), 13.03 (bs, 1H).

Workup

  1. temperatureThe mixture was cooled
  2. filtrationThe precipitate was collected by filtration
  3. washwashed with additional water
  4. customThe solid product was dried under high vacuum

Sources & evidence

ORD record
ord-56d3585aba6046ec9ca6e6b41fe089a3
Source dataset
uspto-grants-2016_02
Patent number
US09247759B2

Reaction notes

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