Hydrazine → HCID 58215597, compound

HRID 1630955Notes

Reaction equation

HRID 1630955 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([CH3:11])[CH:9]=2)[CH:4]=[C:3]1[C:12]1[CH:13]=[C:14]([N:18]2C(=O)C3C(=CC=CC=3)C2=O)[CH:15]=[N:16][CH:17]=1.NN>CCO>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([CH3:11])[CH:9]=2)[CH:4]=[C:3]1[C:12]1[CH:13]=[C:14]([NH2:18])[CH:15]=[N:16][CH:17]=1

Participants

4

Reactant 2

HCID 9321HydrazineHCID 58215615HCID 58215615, compound

Product 1

HCID 58215597HCID 58215597, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A flask is charged with 2-[5-(1,6-dimethyl-1H-indol-2-yl)-pyridin-3-yl]-isoindole-1,3-dione (1.10 g, 2.096 mmol) and EtOH (30 mL). Hydrazine (1.316 mL, 41.9 mmol) is added and the reaction mixture is refluxed for 1 hour. The reaction mixture is cooled to room temperature, filtered and the precipitate is washed thoroughly with ethyl acetate. The filtrate is concentrated in vacuo. The crude is taken up 1M HCl solution and then extracted with EtOAc. The aqueous layer is separated, basified to pH 14 using 4M aqueous NaOH and extracted with DCM thrice. The organic layer is dried over Na2SO4 and concentrated in vacuo to afford 5-(1,6-dimethyl-1H-indol-2-yl)-pyridin-3-ylamine. MS (ESI) m/z 238.4 (M+H)+

Workup

  1. temperaturethe reaction mixture is refluxed for 1 hour
  2. filtrationfiltered
  3. washthe precipitate is washed thoroughly with ethyl acetate
  4. concentrationThe filtrate is concentrated in vacuo
  5. extractionextracted with EtOAc
  6. customThe aqueous layer is separated
  7. extractionextracted with DCM thrice
  8. dry with materialThe organic layer is dried over Na2SO4
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-bb7839a785c34229a0775c8b16556ec4
Source dataset
uspto-grants-2014_07
Patent number
US08791141B2

Reaction notes

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