Hydrochloric Acid → 1-(4-Oxo-cyclohexyl)-1H-pyridin-2-one

HRID 2188545Notes

Reaction equation

HRID 2188545 reaction equation
O1[C:5]2([CH2:10][CH2:9][CH:8]([N:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]3=[O:17])[CH2:7][CH2:6]2)[O:4]CC1.Cl.C(=O)(O)[O-].[Na+]>CC(C)=O>[O:4]=[C:5]1[CH2:10][CH2:9][CH:8]([N:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]2=[O:17])[CH2:7][CH2:6]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 585629001-(1,4-dioxaspiro[4.5]decan-8-yl)pyridin-2(1H)-one

Product 1

HCID 585626631-(4-Oxo-cyclohexyl)-1H-pyridin-2-one

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 1-(1,4-dioxa-spiro[4.5]dec-8-yl)-1H-pyridin-2-one (as prepared in the previous step, ˜300 mg, 1.28 mmol)) in acetone (10 mL) was treated with 1N HCl (2 mL) at room temperature for 4 hours. The reaction was worked up with saturated sodium bicarbonate to adjust the pH to neutral. The solvent was removed in vacuo and residue partitioned between ethyl acetate and water. The organic layer was washed with brine, dried over anhydrous Na2SO4, filtered, concentrated to afford the title compound as white solid.

Workup

  1. customThe solvent was removed in vacuo and residue
  2. custompartitioned between ethyl acetate and water
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-9ab9905baa1c470ca236d29b40e48295
Source dataset
uspto-grants-2012_12
Patent number
US08324186B2

Reaction notes

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