2-Chloro-3-nitropyridine → HCID 67421476, compound

HRID 1799048Notes

Reaction equation

HRID 1799048 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][N:3]=1.Cl[C:11]1[C:16]([N+:17]([O-:19])=[O:18])=[CH:15][CH:14]=[CH:13][N:12]=1>CC(N(C)C)=O>[N+:17]([C:16]1[C:11]([NH:1][C:2]2[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][N:3]=2)=[N:12][CH:13]=[CH:14][CH:15]=1)([O-:19])=[O:18]

Participants

4

Reactant 2

HCID 796132-Chloro-3-nitropyridineHCID 8182602-Amino-5-cyanopyridine

Product 1

HCID 67421476HCID 67421476, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
80 °C

Procedure

To a well stirred solution of 6-aminonicotinonitrile (0.631 g, 5.29 mmol) in dry DMA (10 ml), CS2CO3 (2.157 g, 6.62 mmol) and 2-chloro-3-nitropyridine (0.700 g, 4.415 mmol) were added and reaction mixture was heated at 80° C. under nitrogen atmosphere for 24 h. After completion the reaction mixture was cooled to room temperature, extracted with ethyl acetate (2×100 ml), combined organic layers washed with water (2×50 ml) and brine, dried (Na2SO4), filtered and concentrated under reduced pressure to yield 543 mg of the product.

Workup

  1. customreaction mixture
  2. temperatureAfter completion the reaction mixture was cooled to room temperature
  3. extractionextracted with ethyl acetate (2×100 ml)
  4. washwashed with water (2×50 ml) and brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0f35549325c146aaafc365db46c27253
Source dataset
uspto-grants-2013_01
Patent number
US08344010B2

Reaction notes

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