Hydrazine hydrate (1:1) → HCID 68832119, compound

HRID 1986418Notes

Reaction equation

HRID 1986418 reaction equation
[Br: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>[Br: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 68832494HCID 68832494, compound

Product 1

HCID 68832119HCID 68832119, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2-[(6-bromo-2-isobutyl-4-phenylquinolin-3-yl)methyl]-1H-isoindole-1,3(2H)-dione (1.7 g, 3.4 mmol) in ethanol (150 ml), being heated under reflux, was added hydrazine monohydrate (5 ml, 103 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 (250 ml). The organic layer was washed with saturated aqueous sodium hydrogen carbonate (100 ml) and then saturated brine (100 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-diisopropyl ether to give the title compound (0.90 g, yield 72%) as colorless 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 (250 ml)
  5. washThe organic layer was washed with saturated aqueous sodium hydrogen carbonate (100 ml)
  6. dry with materialsaturated brine (100 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-diisopropyl ether

Sources & evidence

ORD record
ord-1a67b350718b4ad688fea1a0649381bb
Source dataset
uspto-grants-2009_06
Patent number
US07547710B2

Reaction notes

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