Hydrochloric Acid → HCID 19768455, compound

HRID 2248456Notes

Reaction equation

HRID 2248456 reaction equation
S(=O)(=O)(O)O.[CH3:6][C:7]1([CH3:21])[CH2:12][CH2:11][C:10]([C:14]2[CH:15]=[CH:16][C:17](=[O:20])[NH:18][CH:19]=2)(O)[CH2:9][CH2:8]1.[C-]#[N:23].[K+].[ClH:25].FC(F)(F)[C:28]([OH:30])=O>CO.C(OCC)C>[ClH:25].[O:20]=[C:17]1[NH:18][CH:19]=[C:14]([C:10]2([NH:23][CH:28]=[O:30])[CH2:11][CH2:12][C:7]([CH3:21])([CH3:6])[CH2:8][CH2:9]2)[CH:15]=[CH:16]1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 1118Sulfuric AcidHCID 6422Trifluoroacetic acidHCID 9032Potassium CyanideHCID 10242629HCID 10242629, compound

Product 1

HCID 19768455HCID 19768455, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

Concentrated sulfuric acid (54 ml) was added dropwise over 45 minutes to a suspension of 5-(4,4-dimethyl-1-hydroxycyclohexyl)-2(1H)-pyridinone (15 g) and potassium cyanide (13.2 g) in 272 ml of trifluoroacetic acid at 0° C. The resulting suspension was stirred at room temperature for 17 hours and then 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, yielding a foam, which was dissolved in methanol and acidified with ethereal HCl. The volume of solvent was reduced in vacuo, and the precipitated solid (7.1 g) was collected and used in subsequent reactions without further purification.

Workup

  1. temperaturecooled 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. customyielding a foam, which
  8. customthe precipitated solid (7.1 g) was collected
  9. customused in subsequent reactions without further purification

Sources & evidence

ORD record
ord-e6ba3c19b0c94698bebaff1f3c034cbc
Source dataset
uspto-grants-1991_08
Patent number
US05039809

Reaction notes

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