6-Chloro-3-nitropyridin-2-ylamine → 6-Chloropyridine-2,3-diamine

HRID 496275Notes

Reaction equation

HRID 496275 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([NH2:8])[C:5]([N+:9]([O-])=O)=[CH:4][CH:3]=1>C(O)(=O)C.CO.[Zn]>[Cl:1][C:2]1[N:7]=[C:6]([NH2:8])[C:5]([NH2:9])=[CH:4][CH:3]=1

Participants

5

Reactant 1

HCID 27240356-Chloro-3-nitropyridin-2-ylamine

Product 1

HCID 106306156-Chloropyridine-2,3-diamine

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

Add zinc (4.0 g) to a solution of 6-chloro-3-nitropyridin-2-yl-amine (1.0 g, 5.76 mmol) in acetic acid (1.5 mL) and methanol (40 mL). Stir the resulting mixture is at room temperature for 18 hours, and filter through a pad of celite. Evaporate the filtrate to dryness under reduced pressure. Treat the resulting residue with 1N aqueous NaOH and extract with EtOAc. Wash the EtOAc extract with water and saturated aqueous NaCl. Separate the organic layer, dry over Na2SO4, filter and concentrate. Purify by flash column chromatography (50% EtOAc-hexane) to obtain 6-chloro-pyridine-2,3-diamine. C. 5-Chloro-1,3-dihydro-imidazole[4,5-b]pyridin-2-one

Workup

  1. filtrationfilter through a pad of celite
  2. customEvaporate the filtrate to dryness under reduced pressure
  3. additionTreat the resulting residue with 1N aqueous NaOH
  4. extractionextract with EtOAc
  5. washWash the EtOAc
  6. extractionextract with water and saturated aqueous NaCl
  7. customSeparate the organic layer
  8. dry with materialdry over Na2SO4
  9. filtrationfilter
  10. concentrationconcentrate
  11. customPurify by flash column chromatography (50% EtOAc-hexane)

Sources & evidence

ORD record
ord-7b106fa2b74c4929ac883b8499812b9b
Source dataset
uspto-grants-2005_09
Patent number
US06943199B2

Reaction notes

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