2,6-Dichloro-3-nitropyridin-4-amine → 4-Amino-6-chloro-3-nitro-pyridine-2-carbonitrile

HRID 2079523Notes

Reaction equation

HRID 2079523 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[C:4](Cl)[C:3]=1[N+:10]([O-:12])=[O:11].[Cu][C:14]#[N:15]>CN1CCCC1=O.C(OCC)(=O)C.O>[NH2:1][C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[C:4]([C:14]#[N:15])[C:3]=1[N+:10]([O-:12])=[O:11]

Participants

6

Reactant 2

HCID 2827402,6-Dichloro-3-nitropyridin-4-amineHCID 178418546HCID 178418546, compound

Product 1

HCID 552704134-Amino-6-chloro-3-nitro-pyridine-2-carbonitrileYield 23.9%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A stirred suspension of 4-amino-2,6-dichloro-3-nitro-pyridine (17.5 g, 841 mmol) and copper (i) cyanide (15.1 g, 168.3 mmol) in 170 ml of 1-methyl-2-pyrrolidinone was lowered into an oil bath preheated to 180° C. and stirring continued for 12 minutes. The mixture was allowed to cool and diluted with ethyl acetate (700 ml) and water (700 ml) and the resultant suspension filtered. The organic layer was separated and further washed with water (500 ml) and 0.1N HCl (500 ml). The organic layer was then dried over sodium sulfate, filtered and concentrated under reduced pressure to give a brown solid which was washed with diethylether and dichloromethane to afford 4-amino-6-chloro-3-nitro-pyridine-2-carbonitrile (8 g).

Workup

  1. customwas lowered into an oil bath
  2. custompreheated to 180° C.
  3. temperatureto cool
  4. filtrationthe resultant suspension filtered
  5. customThe organic layer was separated
  6. washfurther washed with water (500 ml) and 0.1N HCl (500 ml)
  7. dry with materialThe organic layer was then dried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customto give a brown solid which
  11. washwas washed with diethylether and dichloromethane

Sources & evidence

ORD record
ord-1f775510ad874f888ee20af16bfd9219
Source dataset
uspto-grants-2011_04
Patent number
US07932251B2

Reaction notes

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