Isopropanol → 5-Amino-2,3-dichloropyridine

HRID 1936727Notes

Reaction equation

HRID 1936727 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][C:5]([N+:9]([O-])=O)=[CH:4][N:3]=1.C(O)(C)C>[Fe].O>[NH2:9][C:5]1[CH:6]=[C:7]([Cl:8])[C:2]([Cl:1])=[N:3][CH:4]=1

Participants

5

Reactant 2

HCID 3776IsopropanolHCID 27631062,3-Dichloro-5-nitropyridine

Product 1

HCID 145952195-Amino-2,3-dichloropyridineYield 51.9%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Procedure

2,3-Dichloro-5-nitropyridine (3.9 g) and iron powder (3.0 g) were added to isopropyl alcohol (40 ml) and water (8 ml) and the mixture refluxed for 4 hours. The mixture was then cooled to room temperature and filtered (celite). The filtrate was evaporated under reduced pressure and chromatographed [SiO2; hexane:ethyl acetate (80:20) to (50:50)] to give 5-amino-2,3-dichloropyridine (1.71 g).

Workup

  1. temperaturethe mixture refluxed for 4 hours
  2. filtrationfiltered (celite)
  3. customThe filtrate was evaporated under reduced pressure
  4. customchromatographed [SiO2; hexane:ethyl acetate (80:20) to (50:50)]

Sources & evidence

ORD record
ord-d17b8dc758f3455484c94ab6d92d15b2
Source dataset
uspto-grants-2002_05
Patent number
US06391883B1

Reaction notes

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