Hydrochloric Acid → HCID 19768451, compound

HRID 1196124Notes

Reaction equation

HRID 1196124 reaction equation
S(=O)(=O)(O)O.O[C:7]1([C:13]2[CH:14]=[CH:15][C:16](=[O:20])[N:17]([CH3:19])[CH:18]=2)[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1.[C-]#[N:22].[K+].[ClH:24]>FC(F)(F)C(O)=O.CO.C(OCC)C>[ClH:24].[NH2:22][C:7]1([C:13]2[CH:14]=[CH:15][C:16](=[O:20])[N:17]([CH3:19])[CH:18]=2)[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 1118Sulfuric AcidHCID 9032Potassium CyanideHCID 10104473HCID 10104473, compound

Product 1

HCID 19768451HCID 19768451, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 3283Diethyl EtherSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

Concentrated sulfuric acid (67 ml) was added dropwise over 45 minutes to a suspension of 5-(1-hydroxycyclohexyl)-1-methyl-2(1H)-pyridinone (17.2 g) and potassium cyanide (16.3 g) in 334 ml of trifluoroacetic acid at 0° C. The resulting suspension was stirred at room temperature for 18 hours, and then it was cooled to 0° C., and diethyl ether was added slowly. The solvent was decanted, and the solids were washed with diethyl ether. The product was then dissolved in methanol and neutralized with poly-4-vinylpyridine. The polymer was removed by filtration, and the filtrate concentrated to yield a foam. The foam was dissolved in methanol, acidified with ethereal hydrochloric acid and concentrated, affording 17.1 g of foam.

Workup

  1. temperatureit was cooled to 0° C.
  2. customThe solvent was decanted
  3. washthe solids were washed with diethyl ether
  4. dissolutionThe product was then dissolved in methanol and neutralized with poly-4-vinylpyridine
  5. customThe polymer was removed by filtration
  6. concentrationthe filtrate concentrated
  7. customto yield a foam
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-5def807603264a24ae1698a5fbaa6897
Source dataset
uspto-grants-1992_05
Patent number
US05112981

Reaction notes

Loading…