Ammonia → HCID 5327666, compound

HRID 345699Notes

Reaction equation

HRID 345699 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([C:11]2[C:12](=O)[O:13][C:14](=[O:21])[C:15]=2[C:16]2[CH:20]=[CH:19][NH:18][CH:17]=2)=[CH:3]1.C[N:24](C=O)C.N>O>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([C:11]2[C:12](=[O:13])[NH:24][C:14](=[O:21])[C:15]=2[C:16]2[CH:20]=[CH:19][NH:18][CH:17]=2)=[CH:3]1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 6228DimethylformamideHCID 15113715HCID 15113715, compound

Product 1

HCID 5327666HCID 5327666, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
140 °C

Procedure

135 mg of 3-(1-methyl-3-indolyl)-4-(3-pyrrolyl)furan-2,5-dione were treated with 5 ml of DMF and 5 ml of 33% aqueous ammonia. The solution was heated at 140° C. for 4 hours. The cooled solution was diluted with water and extracted with dichloromethane. The dichloromethane extracts were dried and concentrated. Chromatography of the residue on silica gel with ethyl acetate/hexane (1:1) followed by crystallization from ethyl acetate/hexane gave 50 mg of 3-(1-methyl-3-indolyl)-4-(3-pyrrolyl)-1H-pyrrole-2,5-dione, m.p. 240°-241° C.

Workup

  1. extractionextracted with dichloromethane
  2. dry with materialThe dichloromethane extracts were dried
  3. concentrationconcentrated
  4. customChromatography of the residue on silica gel with ethyl acetate/hexane (1:1) followed by crystallization from ethyl acetate/hexane

Sources & evidence

ORD record
ord-41dfd18e42bc49f28096dc68ceb9798f
Source dataset
uspto-grants-1991_10
Patent number
US05057614

Reaction notes

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