Ammonium Acetate → HCID 14855723, compound

HRID 1769231Notes

Reaction equation

HRID 1769231 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:29])[C:15]=2[C:16]2[C:24]3[C:19](=[CH:20][C:21]([O:27][CH3:28])=[C:22]([O:25][CH3:26])[CH:23]=3)[NH:18][CH:17]=2)=[O:12])=[CH:2]1.C([O-])(=O)C.[NH4+:34]>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:34][C:14](=[O:29])[C:15]=2[C:16]2[C:24]3[C:19](=[CH:20][C:21]([O:27][CH3:28])=[C:22]([O:25][CH3:26])[CH:23]=3)[NH:18][CH:17]=2)=[O:12])=[CH:2]1

Participants

4

Reactant 2

HCID 517165Ammonium AcetateHCID 14855718HCID 14855718, compound

Product 1

HCID 14855723HCID 14855723, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

3.0 g (7.72 mmol) 2-(1H-indol-3-yl)-3-(5,6-dimethoxy-1H-indol-3-yl)-maleic acid anhydride, together with 75 g ammonium acetate, are heated to 140° C. for 1 hour. After cooling, the reaction mixture is mixed with 1.5 l of water and the dark red precipitate is filtered off with suction. There is obtained a crude yield of 2.61 g. For purification, 1.75 g thereof is chromatographed on silica gel with dichloromethane/ethyl acetate (8:1 v/v) as elution agent. There are obtained 1.20 g 2-(1H-indol-3-yl)-3-(5,6-dimethoxy-1H-indol-3-yl)-maleinimide×0.5 ethyl acetate in the form of dark red crystals; m.p. 120° C. (decomp.); RF=0.32 (dichloromethane/ethyl acetate 3:1 v/v). Yield 54% of theory.

Workup

  1. temperatureAfter cooling
  2. filtrationthe dark red precipitate is filtered off with suction
  3. customThere is obtained a crude yield of 2.61 g
  4. customFor purification, 1.75 g
  5. customthereof is chromatographed on silica gel with dichloromethane/ethyl acetate (8:1 v/v) as elution agent

Sources & evidence

ORD record
ord-7860cce343e74422b7378fcd580945e6
Source dataset
uspto-grants-1995_01
Patent number
US05380746

Reaction notes

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