Hydrochloric Acid → HCID 22823472, compound

HRID 2166735Notes

Reaction equation

HRID 2166735 reaction equation
[CH3:1][O:2][C:3]1[C:16]2[C@:15]34[CH2:17][CH2:18][N:19](C=O)[C@@H:9]([C@@H:10]3[CH2:11][CH2:12][C:13]([O:22]C)=[CH:14]4)[CH2:8][C:7]=2[CH:6]=[CH:5][CH:4]=1.Cl>CO>[CH3:1][O:2][C:3]1[C:16]2[C@:15]34[CH2:17][CH2:18][NH:19][C@@H:9]([C@@H:10]3[CH2:11][CH2:12][C:13](=[O:22])[CH2:14]4)[CH2:8][C:7]=2[CH:6]=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 57216533HCID 57216533, compound

Product 1

HCID 22823472HCID 22823472, compoundYield 86.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

600 mg (1.91 mmol) 5,6-didehydro-4,6-dimethoxy-N-formylmorphinan were dissolved in 13.5 ml methanol and 1.5 ml 37% hydrochloric acid were added. This mixture was heated at reflux for 17 h, then the solvent was removed in vacuo, the oily residue dissolved in water and rendered alkaline with 30% NH4OH. After extraction with CHCl3, the organic layer was washed with brine, dried and evaporated to give an oil, which was crystallized with ether to yield 450 mg (81%) 4-methoxymorphinan-6-one. 1 H2O m.p. 136°-138°, [α]D26 -75.7° (c=0.88, CHCl3).

Workup

  1. temperatureThis mixture was heated
  2. temperatureat reflux for 17 h
  3. customthe solvent was removed in vacuo
  4. dissolutionthe oily residue dissolved in water
  5. extractionAfter extraction with CHCl3
  6. washthe organic layer was washed with brine
  7. customdried
  8. customevaporated
  9. customto give an oil, which
  10. customwas crystallized with ether

Sources & evidence

ORD record
ord-122bc93d06f946c58352d0002e2a25c9
Source dataset
uspto-grants-1983_06
Patent number
US04388463

Reaction notes

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