Hydrochloric Acid → 1-(3-Chloropyridin-2-yl)-2-methylpropan-1-one

HRID 2048075Notes

Reaction equation

HRID 2048075 reaction equation
Cl[Mg][CH:3]([CH3:5])[CH3:4].[Cl:6][C:7]1[C:8]([C:13]#N)=[N:9][CH:10]=[CH:11][CH:12]=1.Cl.C1C[O:19]CC1>>[Cl:6][C:7]1[C:8]([C:13](=[O:19])[CH:3]([CH3:5])[CH3:4])=[N:9][CH:10]=[CH:11][CH:12]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 8028Tetrahydrofuran2×HCID 8182583-Chloropyridine-2-carbonitrileHCID 178418918HCID 178418918, compound

Product 1

HCID 578374891-(3-Chloropyridin-2-yl)-2-methylpropan-1-oneYield 15%

Procedure

Chloro(isopropyl)magnesium in THF (35.0 mL, 0.070 mol) was added dropwise to a solution of chloro-2-pyridinecarbonitrile (5.01 g, 0.036 mol) in THF (100 mL) under nitrogen atmosphere at 0° C. It was kept at 0° C. for 2 hours after the addition was complete. The reaction mixture was poured into ice (100 g) and then acidified to pH=3 with an aqueous solution of hydrochloric acid (2.0 M, 100 mL). The product was then extracted with EtOAc (3×100 mL). The organics were combined, dried over sodium sulfate, filtered, and concentrated in vacuo. The resulting crude was purified by silica gel chromatography eluting with 3 to 10% EtOAc in heptane to yield the title compound as a yellow oil (1.98 g, 15% yield):

Workup

  1. additionafter the addition
  2. extractionThe product was then extracted with EtOAc (3×100 mL)
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe resulting crude was purified by silica gel chromatography
  7. washeluting with 3 to 10% EtOAc in heptane

Sources & evidence

ORD record
ord-cc4b7992d9144df5b9263591bdf32388
Source dataset
uspto-grants-2013_11
Patent number
US08592629B2

Reaction notes

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