Hydrochloric Acid → Hydrocodone

HRID 1680243Notes

Reaction equation

HRID 1680243 reaction equation
[CH3:1][N:2]1[C@@H:19]2[CH2:20][C:7]3[CH:8]=[CH:9][C:10]([O:21][CH3:22])=[C:11]4[O:12][C@H:13]5[C:14]([CH:16]=[CH:17][C@@H:18]2[C@:5]5([C:6]=34)[CH2:4][CH2:3]1)=[O:15].Cl.[OH-].[NH4+]>C(O)C.[Pd].O>[O:12]1[C@@H:13]2[C@@:5]34[CH2:4][CH2:3][N:2]([CH3:1])[C@@H:19]([C@@H:18]3[CH2:17][CH2:16][C:14]2=[O:15])[CH2:20][C:7]2=[C:6]4[C:11]1=[C:10]([O:21][CH3:22])[CH:9]=[CH:8]2

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 14923Ammonium HydroxideHCID 5459910Codeinone

Product 1

HCID 5284569HydrocodoneYield 87%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of 1 g of codeinone (prepared by the method of Gavard et al., Bull. Soc. Chim. Fr., 486 (1965)) in 25 ml of 95% ethanol was adjusted to about pH 1 with concentrated hydrochloric acid and was hydrogenated on a Paar apparatus at 50 psi using 200 mg of 10% Palladium on charcoal catalyst for about 1 hour. The catalyst was then removed by filtration and the filtrate was evaporated to give a solid residue. This residue was dissolved in water and the solution adjusted to about pH 11 with concentrated ammonium hydroxide solution. The basic solution was extracted with three portions of chloroform. The combined organic extracts were washed with water, dried over MgSO4 and evaporated to leave a solid residue. The residue was crystallized from absolute ethanol to give the product, which had a melting point of 191°-194° C., in 87% yield.

Workup

  1. customfor about 1 hour
  2. customThe catalyst was then removed by filtration
  3. customthe filtrate was evaporated
  4. customto give a solid residue
  5. extractionThe basic solution was extracted with three portions of chloroform
  6. washThe combined organic extracts were washed with water
  7. dry with materialdried over MgSO4
  8. customevaporated
  9. customto leave a solid residue
  10. customThe residue was crystallized from absolute ethanol
  11. customto give the product, which

Sources & evidence

ORD record
ord-ef1412b59bb74c90a577a9d499b54015
Source dataset
uspto-grants-1981_06
Patent number
US04272541

Reaction notes

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