Triethylamine → 4-Chloro-2-pyridinecarbonitrile

HRID 2361650Notes

Reaction equation

HRID 2361650 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]([NH2:10])=O)[CH:3]=1.CCN(CC)CC.C(OC(C(F)(F)F)=O)(C(F)(F)F)=O>C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]#[N:10])[CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 9845Trifluoroacetic anhydrideHCID 3035434-Chloropyridine-2-carboxamide

Product 1

HCID 6933424-Chloro-2-pyridinecarbonitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of 4-chloropyridine-2-carboxamide (150 mg, 0.96 mmol) in THF (5 ml) at −15° C. was added NEt3 (331 μl, 2.40 mmol) followed by TFAA (150 μl, 1.08 mmol). After stirring for 2 hours at 0° C. the reaction was concentrated then diluted with EtOAc (30 ml) and washed with water (2×15 ml), dried (Na2SO4), filtered and concentrated at reduced pressure. The title compound was obtained as white solid (105 mg, 79%) after purification by FCC.

Workup

  1. concentrationwas concentrated
  2. additionthen diluted with EtOAc (30 ml)
  3. washwashed with water (2×15 ml)
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated at reduced pressure

Sources & evidence

ORD record
ord-6d946f2e950447fbabc309792e23482a
Source dataset
uspto-grants-2014_04
Patent number
US08691804B2

Reaction notes

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