Pyrrolidine → 2-Chloro-6-(pyrrolidin-1-yl)pyridine-4-carbonitrile

HRID 1479824

Reaction equation

HRID 1479824 reaction equation
Cl[C:2]1[CH:7]=[C:6]([C:8]#[N:9])[CH:5]=[C:4]([Cl:10])[N:3]=1.[NH:11]1[CH2:15][CH2:14][CH2:13][CH2:12]1>CCO>[Cl:10][C:4]1[CH:5]=[C:6]([C:8]#[N:9])[CH:7]=[C:2]([N:11]2[CH2:15][CH2:14][CH2:13][CH2:12]2)[N:3]=1

Participants

4

Reactant 2

HCID 31268PyrrolidineHCID 7359062,6-Dichloroisonicotinonitrile

Product 1

HCID 830745802-Chloro-6-(pyrrolidin-1-yl)pyridine-4-carbonitrileYield 87%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

A solution of 2,6-dichloropyridine-4-carbonitrile 24 (4 g, 23.5 mmol) in abs. EtOH (10 mL) was added with pyrrolidine (1.15 mL, 1 mol eq) and the mixture was heated at 70° C. for 6 h. The solvent was removed under reduced pressure, water was added to the residue and the aqueous phase was extracted with EtOAc (3×40 mL). The combined organic phase was washed with brine (1×60 mL), dried over Na2SO4 and evaporated to afford 25A as a pale yellow deliquescent solid (4.2 g, 20 mmol, 87% Yield). 1HNMR (DMSO, 400 MHz) δ 2.00 (m, 4H), 3.42 (m, 4H), 6.39 (s, 1H), 6.61 (s, 1H).

Workup

  1. customThe solvent was removed under reduced pressure, water
  2. additionwas added to the residue
  3. extractionthe aqueous phase was extracted with EtOAc (3×40 mL)
  4. washThe combined organic phase was washed with brine (1×60 mL)
  5. dry with materialdried over Na2SO4
  6. customevaporated

Sources & evidence

ORD record
ord-edd19a8305294f959400d1e5b982b104
Source dataset
uspto-grants-2016_08
Patent number
US09409864B2

Linked notes

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