Diethyl Ether → 2-(1H-Indazol-3-yl)-1H-isoindole-1,3(2H)-dione

HRID 580118Notes

Reaction equation

HRID 580118 reaction equation
O1CCOCC1.[NH2:7][C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[NH:10][N:9]=1.[C:17]1(=O)[O:22][C:20](=[O:21])[C:19]2=[CH:23][CH:24]=[CH:25][CH:26]=[C:18]12.C(OCC)C>O>[C:17]1(=[O:22])[N:7]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[NH:10][N:9]=2)[C:20](=[O:21])[C:19]2=[CH:23][CH:24]=[CH:25][CH:26]=[C:18]12

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 6811Phthalic AnhydrideHCID 133991H-indazol-3-amineHCID 312751,4-Dioxane

Product 1

HCID 27558572-(1H-Indazol-3-yl)-1H-isoindole-1,3(2H)-dioneYield 87%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 50 ml of dioxane were added 5.0 g of 3-aminoindazole 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 8.6 g of 3-phthalimidoindazole having the following analytical values in a yield of 87%.

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-329e63e25bce4dd8a5bb5671c824753d
Source dataset
uspto-grants-1988_06
Patent number
US04751302

Reaction notes

Loading…