Hydrazine hydrate (1:1) → HCID 68832589, compound

HRID 1986415Notes

Reaction equation

HRID 1986415 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([CH2:12][CH:13]([CH3:15])[CH3:14])[C:6]([CH2:16][N:17]1C(=O)C3C(=CC=CC=3)C1=O)=[C:5]2[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.O.NN>C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([CH2:12][CH:13]([CH3:15])[CH3:14])[C:6]([CH2:16][NH2:17])=[C:5]2[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 68828999HCID 68828999, compound

Product 1

HCID 68832589HCID 68832589, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2-[(6-chloro-2-isobutyl-4-phenylquinolin-3-yl)methyl]-1H-isoindole-1,3(2H)-dione (0.54 g, 1.18 mmol) in ethanol (50 ml), being-heated under reflux, was added hydrazine monohydrate (3 ml, 62 mmol), and the mixture was heated under reflux for 2 hrs. The reaction mixture was partitioned between ethyl acetate (100 ml) and saturated aqueous sodium hydrogen carbonate (50 ml)-water (100 ml). The organic layer was washed with saturated aqueous sodium hydrogen carbonate (50 ml) and then saturated brine (20 ml), and dried over anhydrous magnesium sulfate. The solvent was evaporated and the residue was purified by silica gel column chromatography, and crystallized from n-hexane to give the title compound (0.28 g, yield 73%) as pale-yellow crystals.

Workup

  1. temperatureunder reflux
  2. temperaturethe mixture was heated
  3. temperatureunder reflux for 2 hrs
  4. customThe reaction mixture was partitioned between ethyl acetate (100 ml) and saturated aqueous sodium hydrogen carbonate (50 ml)-water (100 ml)
  5. washThe organic layer was washed with saturated aqueous sodium hydrogen carbonate (50 ml)
  6. dry with materialsaturated brine (20 ml), and dried over anhydrous magnesium sulfate
  7. customThe solvent was evaporated
  8. customthe residue was purified by silica gel column chromatography
  9. customcrystallized from n-hexane

Sources & evidence

ORD record
ord-d11ec5f37295447f9555f27eea3b8966
Source dataset
uspto-grants-2009_06
Patent number
US07547710B2

Reaction notes

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