Water → Ethyl 7-chloro-5-methyl-4-oxo-3-phenyl-3,5-dihydro-4H-pyridazino[4,5-b]indole-1-carboxylate

HRID 1937315Notes

Reaction equation

HRID 1937315 reaction equation
[C:1]1([NH:7][NH2:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl:9][C:10]1[CH:18]=[C:17]2[C:13]([C:14]([C:25](=O)[C:26]([O:28][CH2:29][CH3:30])=[O:27])=[C:15]([C:20](OCC)=[O:21])[N:16]2[CH3:19])=[CH:12][CH:11]=1.ClCCl.O>C(O)(=O)C>[Cl:9][C:10]1[CH:11]=[CH:12][C:13]2[C:14]3[C:25]([C:26]([O:28][CH2:29][CH3:30])=[O:27])=[N:8][N:7]([C:1]4[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=4)[C:20](=[O:21])[C:15]=3[N:16]([CH3:19])[C:17]=2[CH:18]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6344DichloromethaneHCID 7516PhenylhydrazineHCID 15461899Ethyl 6-chloro-2-(ethoxycarbonyl)-1-methyl-oxo-1h-indole-3-acetate

Product 1

HCID 15461900Ethyl 7-chloro-5-methyl-4-oxo-3-phenyl-3,5-dihydro-4H-pyridazino[4,5-b]indole-1-carboxylate

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

4 ml (40.6 mmol) of phenylhydrazine are added, at room temperature, to a solution of 4.6 g (13.6 mmol) of ethyl 6-chloro-2-(ethoxycarbonyl)-1-methyl-oxo-1H-indole-3-acetate in 120 ml of acetic acid. The reaction mixture is stirred for 30 min at room temperature and then for 4 h under reflux. The medium is cooled and 350 ml of dichloromethane and 100 ml of water are added. The organic phase is decanted off, washed with a saturated aqueous sodium hydrogen carbonate solution, then with water, dried over sodium sulphate, filtered, concentrated under reduced pressure and the residue purified by chromatography on a silica gel column.

Workup

  1. temperaturefor 4 h under reflux
  2. temperatureThe medium is cooled
  3. customThe organic phase is decanted off
  4. washwashed with a saturated aqueous sodium hydrogen carbonate solution
  5. dry with materialwith water, dried over sodium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customthe residue purified by chromatography on a silica gel column

Sources & evidence

ORD record
ord-77536875ea454292911f129fabec3365
Source dataset
uspto-grants-2002_05
Patent number
US06395729B1

Reaction notes

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