Hydrazine → 2-(2-aminoethyl)-6-phenylpyridazin-3(2H)-one

HRID 1878742Notes

Reaction equation

HRID 1878742 reaction equation
[O:1]=[C:2]1[N:7]([CH2:8][CH2:9][N:10]2C(=O)C3C(=CC=CC=3)C2=O)[N:6]=[C:5]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:4]=[CH:3]1.NN>CO>[NH2:10][CH2:9][CH2:8][N:7]1[C:2](=[O:1])[CH:3]=[CH:4][C:5]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[N:6]1

Participants

4

Reactant 2

HCID 9321HydrazineHCID 13103521HCID 13103521, compound

Product 1

HCID 129026032-(2-aminoethyl)-6-phenylpyridazin-3(2H)-one

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
75 °C

Procedure

A mixture of 2-(2-(6-oxo-3-phenylpyridazin-1(6H)-yl)ethyl)isoindoline-1,3-dione (2.1 g, 6.1 mmol) and hydrazine (10 mL, 10.0 mmol) (THF) in MeOH (40 mL) was heated to 75° C. A clear solution was formed. After overnight (18 h), the slurry was cooled to room temperature and was filtered and washed with MeOH. The filtrate was concentrated and washed with 20% MeOH/CH2Cl2 to give a yellow solid (LCMS indicated the presence of product). The filtrate was concentrated under vacuum and was carried to next step.

Workup

  1. customA clear solution was formed
  2. temperaturethe slurry was cooled to room temperature
  3. filtrationwas filtered
  4. washwashed with MeOH
  5. concentrationThe filtrate was concentrated
  6. washwashed with 20% MeOH/CH2Cl2
  7. customto give a yellow solid (LCMS
  8. concentrationThe filtrate was concentrated under vacuum

Sources & evidence

ORD record
ord-06085f8a8f524b67a71ae8284e771fcb
Source dataset
uspto-grants-2012_11
Patent number
US08314087B2

Reaction notes

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