Water → HCID 57206075, compound

HRID 1414027Notes

Reaction equation

HRID 1414027 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1)([O-:3])=[O:2].[O:11]=[C:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:14](=[O:21])[N:13]1[CH2:22][CH2:23][C:24]1[C:32]2[C:27](=[CH:28][CH:29]=[C:30]([C:33](O)=[O:34])[CH:31]=2)[NH:26][CH:25]=1.O>CN(C)C=O>[O:11]=[C:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:14](=[O:21])[N:13]1[CH2:22][CH2:23][C:24]1[C:32]2[C:27](=[CH:28][CH:29]=[C:30]([C:33]([O:10][C:7]3[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=3)=[O:34])[CH:31]=2)[NH:26][CH:25]=1

Participants

5

Reactant 3

HCID 962WaterHCID 9804-NitrophenolHCID 20289485HCID 20289485, compound

Product 1

HCID 57206075HCID 57206075, compoundYield 61.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

Polyphosphoric acid ethyl ester (40 ml) and 4-nitrophenol (6.3 g) were added to a solution of 3-[2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)ethyl]-1H-indole-5-carboxylic acid (15 g) in dimethylformamide (70 ml) and the mixture was stirred at 80° C. for 24 hours. More polyphosphoric acid ethyl ester (20 ml) was added and the mixture stirred at 80° C. for 3 hours. The mixture was cooled, poured into ice and water (900 ml) and stirred for 1 hour with ice cooling. The resulting solid was filtered off and washed with boiling ethanol (1500 ml) and hot water (600 ml) to give the title compound (12.5 g) as pale yellow crystals m.p. 248°-251° C. T.L.C. Silica, ethyl acetate:2-propanol:water:ammonia (25:15:8:2) Rf 0.9.

Workup

  1. stirringthe mixture stirred at 80° C. for 3 hours
  2. temperatureThe mixture was cooled
  3. stirringstirred for 1 hour with ice cooling
  4. filtrationThe resulting solid was filtered off
  5. washwashed with boiling ethanol (1500 ml) and hot water (600 ml)

Sources & evidence

ORD record
ord-b1739a0f22af45e5ad07e4d996c44562
Source dataset
uspto-grants-1981_02
Patent number
US04252803

Reaction notes

Loading…