Sodium Thiosulfate → (3-Nitro-5-chloro-pyridin-2-yl)-(2,4-dimethyl-pyridin-3-yl)-methanone

HRID 1438543Notes

Reaction equation

HRID 1438543 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N+:18]([O-:20])=[O:19])[C:5]([CH:8]([C:10]2[C:11]([CH3:17])=[N:12][CH:13]=[CH:14][C:15]=2[CH3:16])[OH:9])=[N:6][CH:7]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[O-]S([O-])(=S)=O.[Na+].[Na+].C([O-])(O)=O.[Na+]>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([N+:18]([O-:20])=[O:19])[C:5]([C:8]([C:10]2[C:11]([CH3:17])=[N:12][CH:13]=[CH:14][C:15]=2[CH3:16])=[O:9])=[N:6][CH:7]=1

Participants

6

Reactant 4

HCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 57942234(5-Chloro-3-nitro-pyridin-2-yl)-(2,4-dimethyl-pyridin-3-yl)-methanol

Product 1

HCID 57942081(3-Nitro-5-chloro-pyridin-2-yl)-(2,4-dimethyl-pyridin-3-yl)-methanone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of (5-chloro-3-nitro-pyridin-2-yl)-(2,4-dimethyl-pyridin-3-yl)-methanol (1.46 g) and Dess-Martin periodinane (2.52 g, 5.91 mmol) in CH2Cl2 (15 mL) at room temperature was stirred for 5 h. A mixture of 10% aqueous Na2S2O3 (10 mL) and saturated aqueous NaHCO3 (10 mL) was then added and the biphasic mixture vigorously stirred for 30 min. The phases were then separated and the aqueous portion extracted with CH2Cl2. The combined organic extracts were washed with saturated aqueous NaHCO3, then brine, dried (Na2SO4) and filtered. The filtrate was concentrated under reduced pressure and the residue purified by flash column chromatography over silica gel to provide (5-chloro-3-nitro-pyridin-2-yl)-(2,4-dimethyl-pyridin-3-yl)-methanone. Mass spectrum m/z: 292.3 (M+Na).

Workup

  1. additionwas then added
  2. stirringthe biphasic mixture vigorously stirred for 30 min
  3. customThe phases were then separated
  4. extractionthe aqueous portion extracted with CH2Cl2
  5. washThe combined organic extracts were washed with saturated aqueous NaHCO3
  6. dry with materialbrine, dried (Na2SO4)
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated under reduced pressure
  9. customthe residue purified by flash column chromatography over silica gel

Sources & evidence

ORD record
ord-f57b39806aa847658baf1b9532b3c136
Source dataset
uspto-grants-2009_11
Patent number
US07622583B2

Reaction notes

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