N-methyl-2-pyrrolidone → 6-Chloro-3-nitropyridine-2-carbonitrile

HRID 1048763Notes

Reaction equation

HRID 1048763 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[C:4]([Cl:11])[N:3]=1.[CH3:12][N:13]1CCCC1=O>C(OCC)(=O)C>[Cl:11][C:4]1[N:3]=[C:2]([C:12]#[N:13])[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 13387N-methyl-2-pyrrolidoneHCID 852392,6-Dichloro-3-nitropyridine

Product 1

HCID 133817056-Chloro-3-nitropyridine-2-carbonitrile

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
180 °C

Procedure

2,6-Dichloro-3-nitropyridine (5.18 mmol, 1 g) is mixed with 5 ml of N-methyl-2-pyrrolidinone in a microwave reactor. The reaction mixture is heated at 180° C. for 15 minutes (6 bars). The crude reaction product is dissolved in ethyl acetate, filtered and washed several times using an aqueous phase. The organic phase is collected, dried on magnesium sulfate and dry concentrated. The crude product thus obtained is purified by silica gel chromatography (heptane/AcOEt) to yield, after concentration, 0.62 g (65%) of a brown oil.

Workup

  1. customThe crude reaction product
  2. filtrationfiltered
  3. washwashed several times
  4. customThe organic phase is collected
  5. customdried on magnesium sulfate
  6. customdry
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-7c96834ae0204db99f018e1dca243bfd
Source dataset
uspto-grants-2016_07
Patent number
US09381195B2

Reaction notes

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