HCID 53416990, compound → HCID 53402535, compound

HRID 1697062Notes

Reaction equation

HRID 1697062 reaction equation
[CH3:1][Mg]Cl.[Cl:4][C:5]1[N:16]=[C:15]([CH3:17])[CH:14]=[CH:13][C:6]=1[C:7](N(OC)C)=[O:8]>C1COCC1>[Cl:4][C:5]1[C:6]([C:7](=[O:8])[CH3:1])=[CH:13][CH:14]=[C:15]([CH3:17])[N:16]=1

Participants

4

Reactant 2

HCID 53416990HCID 53416990, compoundHCID 178418332HCID 178418332, compound

Product 1

HCID 53402535HCID 53402535, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A solution of methyl magnesium chloride (3 M in THF, 10 mL) was slowly added at 0° C. to a solution of 2-chloro-N-methoxy-6,N-dimethyl-nicotinamide (2.4 g) in THF (100 mL). The reaction mixture was stirred at 0° C. for 1 h, then quenched with water. The resulting mixture was extracted with EtOAc, the combined organics dried over anhydrous Na2SO4, filtered and evaporated under reduced pressure. The crude residue was purified by flash chromatography (EtOAc/hexane, gradient from 0 to 25% in 25 minutes) to give 1-(2-chloro-6-methylpyridin-3-yl)-ethanone (0.85 g) as a brown oil.

Workup

  1. customquenched with water
  2. extractionThe resulting mixture was extracted with EtOAc
  3. dry with materialthe combined organics dried over anhydrous Na2SO4
  4. filtrationfiltered
  5. customevaporated under reduced pressure
  6. customThe crude residue was purified by flash chromatography (EtOAc/hexane, gradient from 0 to 25% in 25 minutes)

Sources & evidence

ORD record
ord-a56777b8eb8c425a8f87ceb388a3a023
Source dataset
uspto-grants-2012_04
Patent number
US08163906B2

Reaction notes

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