Ammonium Acetate → HCID 14855722, compound

HRID 1769230Notes

Reaction equation

HRID 1769230 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([C:10]2[C:11](O[C:14](=[O:28])[C:15]=2[C:16]2[C:24]3[C:19](=[CH:20][C:21]4OCO[C:22]=4[CH:23]=3)[NH:18][CH:17]=2)=[O:12])=[CH:2]1.[C:29]([O-:32])(=[O:31])C.[NH4+:33]>O>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([C:10]2[C:11]([NH:33][C:14](=[O:28])[C:15]=2[C:16]2[C:24]3[C:19](=[CH:20][C:21]4[O:32][CH2:29][O:31][C:22]=4[CH:23]=3)[NH:18][CH:17]=2)=[O:12])=[CH:2]1

Participants

4

Reactant 2

HCID 517165Ammonium AcetateHCID 14855717HCID 14855717, compound

Product 1

HCID 14855722HCID 14855722, compoundYield 51.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

0.8 g (2.1 mmol) 2-(1H-indol-3-yl)-3-(5,6-methylenedioxy-1H-indol-3-yl)-maleic acid anhydride, together with 20 g ammonium acetate, are heated for 1 hour to 140° C. (melt). After cooling, the reaction mixture is mixed with water and the red-brown precipitate obtained is filtered off with suction. For purification, it is chromatographed on silica gel with dichloromethane/ethyl acetate (3:1 v/v) as elution agent. There is obtained 0.40 g (45% of theory) 2-(1H-indol-3-yl)-3-(5,6-methylenedioxy-1H-indol-3-yl)maleinimide in the form of red crystals; m.p. 150° C. (decomp.); RF=0.4 (methylene chloride/ethyl acetate 3:1 v/v).

Workup

  1. temperatureAfter cooling
  2. customthe red-brown precipitate obtained
  3. filtrationis filtered off with suction
  4. customFor purification, it
  5. customis chromatographed on silica gel with dichloromethane/ethyl acetate (3:1 v/v) as elution agent

Sources & evidence

ORD record
ord-6c48340dd4664fefb513a81a233a4dc3
Source dataset
uspto-grants-1995_01
Patent number
US05380746

Reaction notes

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