Sodium Dithionite → HCID 15622494, compound

HRID 1199934Notes

Reaction equation

HRID 1199934 reaction equation
[C:1]([C:3]1[C:12](=[O:13])[N:11]2[C:6]([CH:7]=[CH:8][CH:9]=[CH:10]2)=[C:5]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:4]=1[C:19]1[CH:24]=[CH:23][C:22]([N+:25]([O-])=O)=[CH:21][CH:20]=1)#[N:2].S(S([O-])=O)([O-])=O.[Na+].[Na+]>C(O)C.CC(C)=O.O>[NH2:25][C:22]1[CH:23]=[CH:24][C:19]([C:4]2[C:5]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[C:6]3[N:11]([C:12](=[O:13])[C:3]=2[C:1]#[N:2])[CH:10]=[CH:9][CH:8]=[CH:7]3)=[CH:20][CH:21]=1

Participants

6

Reactant 2

HCID 24489Sodium DithioniteHCID 15622480HCID 15622480, compound

Product 1

HCID 15622494HCID 15622494, compoundYield 43.6%

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a stirred solution of 100 mg of 3-cyano-1-ethoxycarbonyl-2-(4-nitrophenyl)-4H-quinolizin-4-one (S-20) in 10 ml of ethanol and 5 ml of acetone was added dropwise a solution of 240 mg of sodium hydrosulfite in 5ml of water during 10 minutes. The reaction mixture was heated under reflux for 1 hour and poured into ice-water. The solution was extracted with dichloromethane and the organic layer was dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the residue was recrystallized from methanol to obtain 40 mg of 2-(4-aminophenyl)-3-cyano-1-ethoxycarbonyl-4H-quinolizin-4-one.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 1 hour
  3. extractionThe solution was extracted with dichloromethane
  4. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue was recrystallized from methanol

Sources & evidence

ORD record
ord-7f62bfe5aedf43f1b628bd09127de829
Source dataset
uspto-grants-1990_02
Patent number
US04904657

Reaction notes

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