Acetonitrile → HCID 86656055, compound

HRID 1260318Notes

Reaction equation

HRID 1260318 reaction equation
[H-].[Na+].CO[C:5]([C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([Cl:13])[N:8]=1)=[O:6].[C:14](#[N:16])[CH3:15].C(Cl)Cl.CO>C1(C)C=CC=CC=1>[Cl:13][C:9]1[N:8]=[C:7]([C:5](=[O:6])[CH2:15][C:14]#[N:16])[CH:12]=[CH:11][CH:10]=1

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 24758Sodium hydrideHCID 242723Methyl 6-chloropicolinateHCID 21226129Dichloromethane methanol

Product 1

HCID 86656055HCID 86656055, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A suspension of NaH (1.03 g, 26 mmol; 60% in mineral oil) in toluene (30 ml) was heated to 65° under an argon atmosphere. A solution of 6-chloro-pyridine-2-carboxylic acid methyl ester (4.4 g, 26 mmol) and acetonitrile (1.33 ml, 26 mmol) in toluene (20 ml; heating was required to dissolve the ester) was then added dropwise (exothermic), and the mixture was stirred at 65° for 24 h (compact slurry). After cooling to r.t., ice water was added while stirring. The aqueous phase was collected, washed with Et2O, neutralized with HCl, extracted with CH2Cl2, dried over MgSO4, filtered and evaporated. The product was obtained after silica gel chromatography using a CH2Cl2/MeOH gradient (2.04 g, 40%) as brown solid.

Workup

  1. temperaturewas heated to 65° under an argon atmosphere
  2. temperatureheating
  3. additionwas then added dropwise (exothermic)
  4. stirringwhile stirring
  5. customThe aqueous phase was collected
  6. washwashed with Et2O
  7. extractionextracted with CH2Cl2
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. customevaporated
  11. customThe product was obtained after silica gel chromatography

Sources & evidence

ORD record
ord-600b9418d9674baf93a9393b0bc12854
Source dataset
uspto-grants-2013_06
Patent number
US08470820B2

Reaction notes

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