Hydrochloric Acid → HCID 54570856, compound

HRID 361558Notes

Reaction equation

HRID 361558 reaction equation
[Cl:1][C:2]1[C:3]([S:16][CH3:17])=[N:4][C:5]([CH:11]=[CH:12]N(C)C)=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=1.Cl.C(=O)([O-])[OH:20].[Na+].[BH4-].[Na+]>COCCOC.O>[Cl:1][C:2]1[C:3]([S:16][CH3:17])=[N:4][C:5]([CH2:11][CH2:12][OH:20])=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 54409687HCID 54409687, compound

Product 1

HCID 54570856HCID 54570856, compoundYield 44%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 80711,2-DimethoxyethaneSolvent

Procedure

3-Chloro-6-[2-(dimethylamino)ethenyl]-2-methylthio-5-nitropyridine (D10) (1.05 g, 3.84 mmol) was dissolved in DME (40 ml) and treated with 2.5M hydrochloric acid (8 ml). After 15h, the reaction mixture was treated with solid sodium hydrogen carbonate until pH7 was reached. Water (20 ml) was then added and the resultant mixture was cooled to 0° C. Sodium borohydride (0.581 g, 15.36 mmol) was added portionwise over 2-3 minutes with stirring. After 0.5 h, water (200 ml) was added, and the reaction mixture was extracted with ethyl acetate (3×100 ml). The combined organic extracts were then dried (Na2SO4) and evaporated under reduced pressure to give a red/brown solid, which was purified by silica gel chromatography (3:1 petrol: EtOAc as eluant) to give the title compound as an orange solid (0.420 g, 44%).

Workup

  1. extractionthe reaction mixture was extracted with ethyl acetate (3×100 ml)
  2. dry with materialThe combined organic extracts were then dried (Na2SO4)
  3. customevaporated under reduced pressure
  4. customto give a red/brown solid, which
  5. customwas purified by silica gel chromatography (3:1 petrol: EtOAc as eluant)

Sources & evidence

ORD record
ord-9ca049290c0f44a5b3217a1f3d71b8f5
Source dataset
uspto-grants-1999_02
Patent number
US05866586

Reaction notes

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