Hydrochloric Acid → HCID 19768447, compound

HRID 2248455Notes

Reaction equation

HRID 2248455 reaction equation
S(=O)(=O)(O)O.O[C:7]1([C:13]2[CH:14]=[CH:15][C:16](=[O:19])[NH:17][CH:18]=2)[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1.[C-]#[N:21].[K+].[ClH:23].FC(F)(F)[C:26]([OH:28])=O>CO.C(OCC)C>[ClH:23].[O:19]=[C:16]1[NH:17][CH:18]=[C:13]([C:7]2([NH:21][CH:26]=[O:28])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]2)[CH:14]=[CH:15]1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 1118Sulfuric AcidHCID 6422Trifluoroacetic acidHCID 9032Potassium CyanideHCID 10262021HCID 10262021, compound

Product 1

HCID 19768447HCID 19768447, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

Concentrated sulfuric acid (150 ml) was added dropwise over 45 minutes to a suspension of 5-(1-hydroxycyclohexyl)-2(1H)-pyridinone (37.0 g) and potassium cyanide (370 g) in 770 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 was concentrated to yield a white foam, which was dissolved in methanol and acidified with ethereal HCl. The solvent was removed in vacuo to afford a foam (43.2 g) which was 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 was concentrated
  7. customto yield a white foam, which
  8. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-f6380924085946f1b415e4c713b505d3
Source dataset
uspto-grants-1991_08
Patent number
US05039809

Reaction notes

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