Sodium Iodide → HCID 84819635, compound

HRID 1469711Notes

Reaction equation

HRID 1469711 reaction equation
[CH2:1]([O:3][C:4](=[O:13])[C:5]1[C:10]([Cl:11])=[CH:9][CH:8]=[C:7](Cl)[N:6]=1)[CH3:2].[Na+].[I-:15].C(Cl)(=O)C>CC#N.CCOC(C)=O>[Cl:11][C:10]1[C:5]([C:4]([O:3][CH2:1][CH3:2])=[O:13])=[N:6][C:7]([I:15])=[CH:8][CH:9]=1

Participants

6

Reactant 3

HCID 5238Sodium IodideHCID 6367Acetyl chlorideHCID 45278327Ethyl 3,6-dichloropyridine-2-carboxylate

Product 1

HCID 84819635HCID 84819635, compoundYield 26.8%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 3,6-dichloropicolinic acid ethyl ester (5.0 g, 24 mmol) in CH3CN (45 mL) was added NaI (10 g, 66.7 mmol) and acetyl chloride (2.5 mL). The reaction mass was heated in a sealed tube at 100° C. for 48 h. The reaction mass was diluted with EtOAc and was washed with saturated solutions of Na2S2O3 and NaHCO3. The organic layer was separated, dried, filtered and concentrated to afford 2 g of the title product. 1H NMR (300 MHz, DMSO-d6): δ 8.04 (d, J=8.4 Hz, 1H), 7.82 (d, J=8.7 Hz, 1H), 4.38 (q, J=7.5 Hz, 2H), 1.32 (t, J=6.9 Hz, 3H).

Workup

  1. washwas washed with saturated solutions of Na2S2O3 and NaHCO3
  2. customThe organic layer was separated
  3. customdried
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-1740d887c8be4c6d890c509bbc2220f4
Source dataset
uspto-grants-2015_04
Patent number
US09006257B2

Reaction notes

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