Water → 2-[2-(1H-indol-3-yl)ethyl]-1H-Isoindole-1,3(2H)-dione

HRID 1095511Notes

Reaction equation

HRID 1095511 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][CH:5]=1.[C:13]1(=O)[O:18][C:16](=[O:17])[C:15]2=[CH:19][CH:20]=[CH:21][CH:22]=[C:14]12.O>C1(C)C=CC=CC=1>[NH:6]1[C:7]2[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:4]([CH2:3][CH2:2][N:1]2[C:16](=[O:17])[C:15]3[C:14](=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:13]2=[O:18])=[CH:5]1

Participants

5

Reactant 3

HCID 962WaterHCID 1150TryptamineHCID 6811Phthalic Anhydride

Product 1

HCID 2885772-[2-(1H-indol-3-yl)ethyl]-1H-Isoindole-1,3(2H)-dione

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of tryptamine (3.04 g, 19.0 mmol) and phthalic anhydride (3.0 g, 20.0 mmol) in toluene (300 ml) was boiled under reflux for 12 h using a water separator. The solvent was removed i. vac. and the residue was recrystallized from methylene chloride/cyclohexane. Yield: 4.46 g (81%)

Workup

  1. temperatureunder reflux for 12 h
  2. customThe solvent was removed i
  3. customand the residue was recrystallized from methylene chloride/cyclohexane

Sources & evidence

ORD record
ord-10e4f6e9b27f4f91a28a43a56083ab90
Source dataset
uspto-grants-2012_03
Patent number
US08138187B2

Reaction notes

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