2,3-Dichloro-5-nitropyridine → 5-Amino-2,3-dichloropyridine

HRID 464623Notes

Reaction equation

HRID 464623 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][C:5]([N+:9]([O-])=O)=[CH:4][N:3]=1>Cl>[NH2:9][C:5]1[CH:6]=[C:7]([Cl:8])[C:2]([Cl:1])=[N:3][CH:4]=1

Participants

3

Reactant 1

HCID 27631062,3-Dichloro-5-nitropyridine

Product 1

HCID 145952195-Amino-2,3-dichloropyridineYield 51.4%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
5 °C

Procedure

2,3-Dichloro-5-nitropyridine (50.0 g, 0.26 mol) was dissolved in 500 ml conc. HCl, and the solution cooled to 5° C. Stannous chloride dihydrate (160 g) was added over 30 minutes. The reaction was stirred for 2 hours at 5° C. and then heated on a stram bath for 90 minutes. The mixture was cooled and extracted with ethyl acetate. The organic fractions were washed with 10 percent sodium hydroxide, then dried over anhydrous magnesium sulfate, and the solvent evaporated in vacuo to give 21.8 g (50 percent) of the amine, m.p. 110°-113° C.

Workup

  1. temperatureheated on a stram bath for 90 minutes
  2. temperatureThe mixture was cooled
  3. extractionextracted with ethyl acetate
  4. washThe organic fractions were washed with 10 percent sodium hydroxide
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent evaporated in vacuo

Sources & evidence

ORD record
ord-b5dfbfd73a814877b6b89f7b8a43bb41
Source dataset
uspto-grants-1985_10
Patent number
US04548888

Reaction notes

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