Diethyl Ether → 2-(4-chloro-1H-indazol-3-yl)isoindoline-1,3-dione

HRID 484838Notes

Reaction equation

HRID 484838 reaction equation
O1CCOCC1.[NH2:7][C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][C:15]=2[Cl:17])[NH:10][N:9]=1.[C:18]1(=O)[O:23][C:21](=[O:22])[C:20]2=[CH:24][CH:25]=[CH:26][CH:27]=[C:19]12.C(OCC)C>O>[C:18]1(=[O:23])[N:7]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][C:15]=3[Cl:17])[NH:10][N:9]=2)[C:21](=[O:22])[C:20]2=[CH:24][CH:25]=[CH:26][CH:27]=[C:19]12

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 6811Phthalic AnhydrideHCID 312751,4-DioxaneHCID 3134443-Amino-4-chloroindazole

Product 1

HCID 132297712-(4-chloro-1H-indazol-3-yl)isoindoline-1,3-dioneYield 99.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 50 ml of dioxane were added 5.66 g of 3-amino-4-chloroindazole thus obtained and 6.68 g of phthalic anhydride, and the mixture was stirred for 5 hours at 120° C. After the mixture was condensed under reduced pressure, the condensed residue was added with 30 ml of diethyl ether and stirred under cooling with ice and water for 30 minutes to separate crystals. Then the crystals were obtained by filtration and dried under reduced pressure to give 9.96 g of 3-phthalimido-4-chloroindazole having the following analytical values in a yield of 89%.

Workup

  1. customthus obtained
  2. customcondensed under reduced pressure
  3. customto separate crystals
  4. customThen the crystals were obtained by filtration
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-76887bfddce0478db86a0d78c7793574
Source dataset
uspto-grants-1985_08
Patent number
US04533731

Reaction notes

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