Water → 5-Amino-2,3-dichloropyridine

HRID 845180Notes

Reaction equation

HRID 845180 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][C:5]([N+:9]([O-])=O)=[CH:4][N:3]=1.O>C(O)(=O)C.[Fe]>[NH2:9][C:5]1[CH:4]=[N:3][C:2]([Cl:1])=[C:7]([Cl:8])[CH:6]=1

Participants

5

Reactant 2

HCID 962WaterHCID 27631062,3-Dichloro-5-nitropyridine

Product 1

HCID 145952195-Amino-2,3-dichloropyridine

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Procedure

77.2 g (0.4 mol) of 2,3-dichloro-5-nitropyridine were dissolved in 135 ml of glacial acetic acid, and 800 ml of water were added with stirring. 111.7 g (2 mol) of iron powder were introduced in portions into the mixture (temperature≤50° C.). After completion of the reaction, the mixture is filtered under suction and the product extracted using ethyl acetate. The organic phase was washed with water until neutral, dried using MgSO4 and concentrated by evaporation. The product was recrystallized from toluene.

Workup

  1. customAfter completion of the reaction
  2. filtrationthe mixture is filtered under suction
  3. extractionthe product extracted
  4. washThe organic phase was washed with water until neutral,
  5. customdried
  6. concentrationconcentrated by evaporation
  7. customThe product was recrystallized from toluene

Sources & evidence

ORD record
ord-5cf77ae605d34ccf94a5f3f73d2cdf76
Source dataset
uspto-grants-1988_07
Patent number
US04756739

Reaction notes

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