Sodium dithionate → 2-chloro-N4-prop-2-ynylquinoline-3,4-diamine

HRID 606039Notes

Reaction equation

HRID 606039 reaction equation
S(S([O-])(=O)=O)([O-])(=O)=O.[Na+].[Na+].[Cl:11][C:12]1[C:21]([N+:22]([O-])=O)=[C:20]([NH:25][CH2:26][C:27]#[CH:28])[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[N:13]=1>C(O)C.C(#N)C>[Cl:11][C:12]1[C:21]([NH2:22])=[C:20]([NH:25][CH2:26][C:27]#[CH:28])[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[N:13]=1

Participants

5

Reactant 2

HCID 146045Sodium dithionateHCID 862475782-chloro-3-nitro-N-prop-2-ynylquinolin-4-amine

Product 1

HCID 862475812-chloro-N4-prop-2-ynylquinoline-3,4-diamineYield 62%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6342AcetonitrileSolvent

Procedure

An aqueous solution (1.5 L) of sodium dithionate (265 g, 1.52 mol) was added to a solution of 2-chloro-3-nitro-N-prop-2-ynylquinolin-4-amine (79.3 g, 0.303 mol) in ethanol (750 mL) and acetonitrile (950 mL). A fine white precipitate formed within seconds. The reaction was worked-up after thin layer chromatography (TLC) analysis of the reaction mixture indicated that the reaction was complete. The solids were removed by filtration and the filter cake was rinsed with dichloromethane. The filtrate was concentrated under reduced pressure to remove the volatiles, leaving an aqueous solution that was extracted with several portions of dichloromethane. The organic layers were combined, washed with brine, dried over magnesium sulfate, filtered, and concentrated to yield 2-chloro-N4-prop-2-ynylquinoline-3,4-diamine (43.5 g) that was approximately 60% pure and was used without further purification.

Workup

  1. customA fine white precipitate formed within seconds
  2. customThe solids were removed by filtration
  3. washthe filter cake was rinsed with dichloromethane
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customto remove the volatiles
  6. customleaving an aqueous solution that
  7. extractionwas extracted with several portions of dichloromethane
  8. washwashed with brine
  9. dry with materialdried over magnesium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-9e35c2ea9fa64542858cf5d8c7ad5e78
Source dataset
uspto-grants-2011_03
Patent number
US07915281B2

Reaction notes

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