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

HRID 606051Notes

Reaction equation

HRID 606051 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][CH2:27][CH2:28][C:29]#[CH:30])[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[N:13]=1>C(O)C.C(#N)C.O>[Cl:11][C:12]1[C:21]([NH2:22])=[C:20]([NH:25][CH2:26][CH2:27][CH2:28][C:29]#[CH:30])[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[N:13]=1

Participants

6

Reactant 2

HCID 146045Sodium dithionateHCID 862475932-chloro-3-nitro-N-pent-4-ynylquinolin-4-amine

Product 1

HCID 862475962-chloro-N4-pent-4-ynylquinoline-3,4-diamineYield 71.5%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

An aqueous solution (125 mL) of sodium dithionate (38.0 g, 218 mmol) was added to a solution of 2-chloro-3-nitro-N-pent-4-ynylquinolin-4-amine (12.64 g, 43.63 mmol) in ethanol (15 mL) and acetonitrile (130 mL). A fine white precipitate formed within seconds. After 2.5 hours, the volatiles were removed under reduced pressure leaving a yellow aqueous mixture that was diluted with water (1 L) and washed with dichloromethane (250 mL×3). The organic layers were combined, washed with water and brine, dried over magnesium sulfate, filtered, and concentrated to yield 2-chloro-N4-pent-4-ynylquinoline-3,4-diamine as an amber oil (8.10 g) that was used without further purification.

Workup

  1. customA fine white precipitate formed within seconds
  2. customthe volatiles were removed under reduced pressure
  3. customleaving a yellow aqueous mixture that
  4. washwashed with dichloromethane (250 mL×3)
  5. washwashed with water and brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-88c16d6f10c041429e6bd5d49e7556da
Source dataset
uspto-grants-2011_03
Patent number
US07915281B2

Reaction notes

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