Water → HCID 86692223, compound

HRID 1469712Notes

Reaction equation

HRID 1469712 reaction equation
[Cl:1][C:2]1[C:3]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[N:4][C:5](I)=[CH:6][CH:7]=1.[C:14]([Cu])#[N:15].O>N1C=CC=CC=1>[Cl:1][C:2]1[C:3]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[N:4][C:5]([C:14]#[N:15])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 84819635HCID 84819635, compoundHCID 178418546HCID 178418546, compound

Product 1

HCID 86692223HCID 86692223, compoundYield 75.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of ethyl 3-chloro-6-iodopicolinate (1.6 g, 5.38 mmol) in pyridine (40 mL) was added CuCN (480 mg, 5.36 mmol). The reaction mass was heated at 80° C. for 6 h. Then water was added to the reaction mass and it was extracted with EtOAc. The organic layer was separated, dried, filtered and concentrated to afford 850 mg of the title product. 1H NMR (300 MHz, DMSO-d6): δ 8.44 (d, J=8.1 Hz, 1H), 8.28 (d, J=8.4 Hz, 1H), 4.42 (q, J=7.2 Hz, 2H), 1.33 (t, J=7.2 Hz, 3H).

Workup

  1. extractionwas extracted with EtOAc
  2. customThe organic layer was separated
  3. customdried
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-71047d4a60ae4fdc96c29b80ae5c3ba1
Source dataset
uspto-grants-2015_04
Patent number
US09006257B2

Reaction notes

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