Hydrazine → HCID 21254045, compound

HRID 1531541Notes

Reaction equation

HRID 1531541 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][C:14]([OH:31])=[CH:13][CH:12]=3)[CH:5]=[C:6]([CH3:8])[CH:7]=1.NN>C(O)C.O1CCCC1>[NH2:20][CH2:19][CH2:18][C:17]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([OH:31])[CH:15]=2)[NH:10][C:9]=1[C:4]1[CH:3]=[C:2]([CH3:1])[CH:7]=[C:6]([CH3:8])[CH:5]=1

Participants

5

Reactant 2

HCID 9321HydrazineHCID 21254080HCID 21254080, compound

Product 1

HCID 21254045HCID 21254045, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-[2-[2-(3,5-dimethylphenyl)-5-hydroxy-1H-indol-3-yl]ethyl]isoindole-1,3-dione (418 mg in a mixture of 7 mL ethanol and 7 mL tetrahydrofuran) was added 2.5 mL of 95% aqueous hydrazine and the reaction stirred at room temperature. After 12 hours the mixture was concentrated in vacuo and purified by flash chromatography on silica gel (methylene chloride:methanol:ammonium hydroxide, 89:11:1) to provide the title compound (228 mg).

Workup

  1. concentrationAfter 12 hours the mixture was concentrated in vacuo
  2. custompurified by flash chromatography on silica gel (methylene chloride:methanol:ammonium hydroxide, 89:11:1)

Sources & evidence

ORD record
ord-3e1c9d2647cc4d9591b98d05d00e2463
Source dataset
uspto-grants-2001_03
Patent number
US06197975B1

Reaction notes

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