HCID 13491246, compound → HCID 13491250, compound

HRID 1719619Notes

Reaction equation

HRID 1719619 reaction equation
C([NH:4][CH:5]1[CH:12]2[C:13](=[O:24])[C:14]3[CH:19]=[CH:18][C:17]([O:20]C(=O)C)=[CH:16][C:15]=3[C:6]1([CH3:25])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11]2)(=O)C>C(O)C.Cl>[NH2:4][CH:5]1[CH:12]2[C:13](=[O:24])[C:14]3[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][C:15]=3[C:6]1([CH3:25])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11]2

Participants

4

Reactant 1

HCID 13491246HCID 13491246, compound

Product 1

HCID 13491250HCID 13491250, compoundYield 65%

Reagents, catalysts & solvents 2

HCID 702EthanolCatalystHCID 313Hydrochloric AcidSolvent

Procedure

13-Acetylamino-6,7,8,9,10,11-hexahydro-3-acetoxy-5-methyl-5,11-methanobenzocyclodecen-12(5H)-one (3 g., 0.008 mole) was refluxed with 10 mL of 20% hydrochloric acid in the presence of a few drops of ethanol for 24 hours. The reaction mixture was boiled with 0.5 g. of charcoal, filtered and the solvent was evaporated under reduced pressure. The remaining solid was recrystallized from acetone-ethanol (5:1) to afford 1.5 g. (65% yield) of the title compound as a hydrochloride dihydrate, mp 256°-258° C.

Workup

  1. filtrationof charcoal, filtered
  2. customthe solvent was evaporated under reduced pressure
  3. customThe remaining solid was recrystallized from acetone-ethanol (5:1)
  4. customto afford 1.5 g

Sources & evidence

ORD record
ord-9e23c4f2c93f42aeb1b16e24ca823561
Source dataset
uspto-grants-1985_09
Patent number
US04540806

Reaction notes

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