Phthalic Acid → 2-(1H-Indazol-3-yl)-1H-isoindole-1,3(2H)-dione

HRID 1381308Notes

Reaction equation

HRID 1381308 reaction equation
[NH2:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[NH:4][N:3]=1.[C:11](O)(=[O:21])[C:12]1[C:13](=[CH:17][CH:18]=[CH:19][CH:20]=1)[C:14](O)=[O:15].O1CCOCC1.C(OCC)C>O>[C:11]1(=[O:21])[N:1]([C:2]2[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[NH:4][N:3]=2)[C:14](=[O:15])[C:13]2=[CH:17][CH:18]=[CH:19][CH:20]=[C:12]12

Participants

6

Reactant 4

HCID 1017Phthalic AcidHCID 3283Diethyl EtherHCID 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

Conditions

Temperature
120 °C

Procedure

5.0 g of the same 3-aminoindazole as Example 1 and 6.68 g of phthalic acid were added to 50 ml of dioxane, and the mixture was stirred for 5 hours at 120° C. The mixture was condensed under reduced pressure, 30 ml of diethyl ether was added and the mixture was stirred under cooling with ice and water for 30 minutes to separate crystals. The crystals were obtained by filtration and dried under reduced pressure to give 8.6 g of 3-phthalimidoindazole in a yield of 87%.

Workup

  1. additionwas added
  2. stirringthe mixture was stirred
  3. customto separate crystals
  4. customThe crystals were obtained by filtration
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-1edf10402f004861afabc92889995064
Source dataset
uspto-grants-1986_04
Patent number
US04585869

Reaction notes

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