Hydrochloric Acid → HCID 53730750, compound

HRID 442754Notes

Reaction equation

HRID 442754 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([O:11]S(C3C=CC=CC=3)(=O)=O)[CH:9]=2)[C:4]([C:21]2[C:22](=[O:37])[NH:23][C:24](=[O:36])[C:25]=2[C:26]2[C:34]3[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=3)[N:28]([CH3:35])[CH:27]=2)=[CH:3]1.[OH-].[Na+].CO.Cl>O>[OH:11][C:8]1[CH:9]=[C:10]2[C:5]([C:4]([C:21]3[C:22](=[O:37])[NH:23][C:24](=[O:36])[C:25]=3[C:26]3[C:34]4[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=4)[N:28]([CH3:35])[CH:27]=3)=[CH:3][N:2]2[CH3:1])=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 54159292HCID 54159292, compound

Product 1

HCID 53730750HCID 53730750, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

3-(6-hydroxy-1-methyl-1H-indol-3-yl)-4-(1-methyl-1H-indol-3-yl)-pyrrole-2,5-dione was prepared by treating Benzenesulfonic acid 1-methyl-3-[4-(1-methyl-1H-indol-3-yl)-2,5-dioxo-2,5-dihydro-1H-pyrrol-3-yl]-1H-indol-6-yl ester (141 mg 0.28 mm) with 4N NaOH (0.5 mL, 2 mmol) and CH3OH (4 mL) and heating to reflux temperature for 6 hours. After cooling to room temperature, the reaction mixture was diluted with H2O, acidified with 2N HCl, and extracted with EtOAc. The organic phase was washed with saturated NaCl solution, dried over MgSO4, filtered and evaporated to afford, after purification by flash column chromatography 3-(6-hydroxy-1-methyl-1H-indol-3-yl)-4-(1-methyl-1H-indol-3-yl)-pyrrole-2,5-dione (15 mg); mp=279°-282° C.

Workup

  1. temperatureheating
  2. temperatureto reflux temperature for 6 hours
  3. extractionextracted with EtOAc
  4. washThe organic phase was washed with saturated NaCl solution
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customevaporated
  8. customto afford
  9. customafter purification by flash column chromatography 3-(6-hydroxy-1-methyl-1H-indol-3-yl)-4-(1-methyl-1H-indol-3-yl)-pyrrole-2,5-dione (15 mg)

Sources & evidence

ORD record
ord-6de721acca244f0e8d4a2e1c48334d5b
Source dataset
uspto-grants-1999_04
Patent number
US05891901

Reaction notes

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