Hydrazine → 2-[2-(3,5-dimethylphenyl)-1H-indol-3-yl]ethylamine

HRID 1292375Notes

Reaction equation

HRID 1292375 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([C:9]2[NH:10][C:11]3[C:16]([C:17]=2[CH2:18][CH2:19][N:20]2C(=O)C4C(=CC=CC=4)C2=O)=[CH:15][CH:14]=[CH:13][CH:12]=3)[CH:5]=[C:6]([CH3:8])[CH:7]=1.NN>O1CCCC1.C(O)C>[CH3:1][C:2]1[CH:3]=[C:4]([C:9]2[NH:10][C:11]3[C:16]([C:17]=2[CH2:18][CH2:19][NH2:20])=[CH:15][CH:14]=[CH:13][CH:12]=3)[CH:5]=[C:6]([CH3:8])[CH:7]=1

Participants

5

Reactant 2

HCID 9321HydrazineHCID 153130482-(2-(2-(3,5-Dimethylphenyl)-1H-indol-3-yl)ethyl)isoindoline-1,3-dione

Product 1

HCID 221009192-[2-(3,5-dimethylphenyl)-1H-indol-3-yl]ethylamine

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-{2-[2-(3,5-dimethylphenyl)-1H-indol-3-yl]-ethyl}-isoindole-1,3-dione (87 mg in a mixture of 4 mL tetrahydrofuran and 4 mL ethanol) was added 0.6 mL of 95% aqueous hydrazine and the reaction stirred at room temperature. After 18 hours the mixture was concentrated in vacuo and purified by flash chromatography on silica gel (methylene chloride:methanol:ammonium hydroxide, 9:6:1) to provide the title compound (54 mg).

Workup

  1. concentrationAfter 18 hours the mixture was concentrated in vacuo
  2. custompurified by flash chromatography on silica gel (methylene chloride:methanol:ammonium hydroxide, 9:6:1)

Sources & evidence

ORD record
ord-a256a552a25e4f29aa80e21284c34cb7
Source dataset
uspto-grants-1998_05
Patent number
US05756507

Reaction notes

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