Acetyl chloride → HCID 66735718, compound

HRID 1641408Notes

Reaction equation

HRID 1641408 reaction equation
Br[C:2]1([C:8]#[N:9])[CH:7]=[CH:6][CH:5]=[CH:4][NH:3]1.C[Mg+].[Br-:12].[C:13](Cl)(=[O:15])[CH3:14].[C:17](=O)(O)[O-].[Na+]>C1COCC1>[Br:12][C:5]1[CH:6]=[CH:7][C:2]([C:8]([NH:9][C:13](=[O:15])[CH3:14])=[CH2:17])=[N:3][CH:4]=1

Participants

6

Reactant 4

HCID 6367Acetyl chlorideHCID 516892Sodium BicarbonateHCID 66735846HCID 66735846, compoundHCID 178418689HCID 178418689, compound

Product 1

HCID 66735718HCID 66735718, compoundYield 22%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 2-bromo-picolinonitrile (25.8 g, 141.0 mmol) in THF (500 ml) was added a solution of MeMgBr (120.8 ml, 169.2 mmol) in THF at 0° C. The reaction was stirred at room temperature for 1.5 hours, followed by dropwise addition of acetyl chloride (15 ml, 211.5 mmol). The reaction mixture was stirred at room temperature for 16 hours. Saturated sodium bicarbonate solution (50 ml) was added and extracted with EtOAc (2×200 ml). The combined organic was dried over sodium sulfate. After removal of solvent, the resulted residue was purified by column chromatography (hexane-EtOAc=2.5:1) to give the title compound as a white solid (7.5 g, 22%). 1H NMR (400 MHz) δ 9.41 (s, 1H), 8.70 (d, J=2.4 Hz, 1H), 8.10 (dd, J=2.4 and 8.4 Hz, 1H), 7.73 (d, J=8.8 Hz, 1H), 6.02 (s, 1H), 5.59 (s, 1H), 2.07 (s, 3H). MS: Calcd.: 240. Found: [M+H]+ 241.

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 16 hours
  2. extractionextracted with EtOAc (2×200 ml)
  3. dry with materialThe combined organic was dried over sodium sulfate
  4. customAfter removal of solvent
  5. customthe resulted residue was purified by column chromatography (hexane-EtOAc=2.5:1)

Sources & evidence

ORD record
ord-5d4fa6b76bac4d0dbc36b9488633ff31
Source dataset
uspto-grants-2012_02
Patent number
US08114989B2

Reaction notes

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