Phthalic Anhydride → HCID 2755705, compound

HRID 1686270Notes

Reaction equation

HRID 1686270 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-71608d3c7b4f4bb48c375327626843e0
Source dataset
uspto-grants-2012_04
Patent number
US08148544B2

Reaction notes

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