HCID 54510944, compound → HCID 53665351, compound

HRID 361556Notes

Reaction equation

HRID 361556 reaction equation
[Cl:1][C:2]1[C:3]([S:14][CH3:15])=[N:4][CH:5]=[C:6]([N+:11]([O-])=O)[C:7]=1[CH2:8][CH2:9][OH:10]>C(O)(=O)C.O.[Fe]>[NH2:11][C:6]1[C:7]([CH2:8][CH2:9][OH:10])=[C:2]([Cl:1])[C:3]([S:14][CH3:15])=[N:4][CH:5]=1

Participants

5

Reactant 1

HCID 54510944HCID 54510944, compound

Product 1

HCID 53665351HCID 53665351, compound

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

3-Chloro-4-(2-hydroxyethyl)-2-methylthio-5-nitropyridine (0.430 g, 1.73 mmol) was dissolved in a mixture of glacial acetic acid (30 ml) and water (15 ml), and was treated with iron powder (3.78 g, 0.068 mol) with stirring. After 0.5 h, the mixture was filtered through kieselguhr and the resultant yellow solution was evaporated under reduced pressure. The residue was partitioned between sodium bicarbonate solution and ethyl acetate. The biphasic suspension was filtered through kieselguhr, and the organic layer was dried (Na2SO4) and evaporated under reduced pressure to give the title compound as a yellow solid, which was dried in vacuo (0.275 g, 73%).

Workup

  1. filtrationthe mixture was filtered through kieselguhr
  2. customthe resultant yellow solution was evaporated under reduced pressure
  3. customThe residue was partitioned between sodium bicarbonate solution and ethyl acetate
  4. filtrationThe biphasic suspension was filtered through kieselguhr
  5. dry with materialthe organic layer was dried (Na2SO4)
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-d294a76a1004421c93d22c338d972f08
Source dataset
uspto-grants-1999_02
Patent number
US05866586

Reaction notes

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