Formaldehyde → 1-hydroxymethyl-3-(1-methyl-1H-indol-3-yl)-4-(1-methyl-6-nitro-1H-indol-3-yl)-pyrrole-2,5-dione

HRID 411767

Reaction equation

HRID 411767 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:30])[NH:13][C:14](=[O:29])[C:15]=2[C:16]2[C:24]3[C:19](=[CH:20][C:21]([N+:25]([O-:27])=[O:26])=[CH:22][CH:23]=3)[N:18]([CH3:28])[CH:17]=2)=[CH:3]1.[CH2:31]=[O:32]>O>[OH:32][CH2:31][N:13]1[C:14](=[O:29])[C:15]([C:16]2[C:24]3[C:19](=[CH:20][C:21]([N+:25]([O-:27])=[O:26])=[CH:22][CH:23]=3)[N:18]([CH3:28])[CH:17]=2)=[C:11]([C:4]2[C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[N:2]([CH3:1])[CH:3]=2)[C:12]1=[O:30]

Participants

4

Reactant 2

HCID 712FormaldehydeHCID 53276861H-pyrrole-2,5-dione, 3-(1-methyl-1H-indol-3-yl)-4-(1-methyl-6-nitro-1H-indol-3-yl)-

Product 1

HCID 98673381-hydroxymethyl-3-(1-methyl-1H-indol-3-yl)-4-(1-methyl-6-nitro-1H-indol-3-yl)-pyrrole-2,5-dione

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A suspension consisting of 0.5 g (1.25 mmole) of 3-(1-methyl-3-indolyl)-4-(1-methyl-6-nitro-3-indolyl)-1H-pyrrole-2,5-dione (See Davis U.S. Pat. No. 5,057,614), 4.0 ml of formaldehyde solution (37% w/w), and 2.0 ml of water was heated to 125° C. with stirring and with a reflux condensed attached for 14 hours. The reaction mixture was cooled and diluted with water. The red solid was filtered, washed with water and dried. The solid was purified by chromatography using silica gel and a mixture of EtOAc/Hexane as elutant to afford 1-hydroxymethyl-3-(1-methyl-1H-indol-3-yl)-4-(1-methyl-6-nitro-1H-indol-3-yl)-pyrrole-2,5-dione (mp=209-211° C.).

Workup

  1. temperatureThe reaction mixture was cooled
  2. filtrationThe red solid was filtered
  3. washwashed with water
  4. customdried
  5. customThe solid was purified by chromatography
  6. additiona mixture of EtOAc/Hexane as elutant

Sources & evidence

ORD record
ord-e37221ec8e99449d87195afdb5bf7723
Source dataset
uspto-grants-2003_05
Patent number
US06559164B1

Linked notes

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