HCID 13772986, compound → HCID 13772988, compound

HRID 746007Notes

Reaction equation

HRID 746007 reaction equation
[CH2:1]([N:3]1[C:11]2[CH:10]=[C:9]3[CH:12]=[CH:13][C:14]([O:18][CH3:19])=[C:15]([O:16][CH3:17])[C:8]3=[C:7]3[CH:20]=[C:21]([CH3:23])[CH:22]=[C:5]([C:6]=23)[C:4]1(O)[CH2:24][CH2:25][CH3:26])[CH3:2]>C(O)C.[Zn].[Hg](Cl)Cl>[CH2:1]([N:3]1[C@@H:11]2[C:6]3=[C:7]([CH:20]=[C:21]([CH3:23])[CH:22]=[C:5]3[C@H:4]1[CH2:24][CH2:25][CH3:26])[C:8]1[C:15]([O:16][CH3:17])=[C:14]([O:18][CH3:19])[CH:13]=[CH:12][C:9]=1[CH2:10]2)[CH3:2]

Participants

5

Reactant 1

HCID 13772986HCID 13772986, compound

Product 1

HCID 13772988HCID 13772988, compound

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 24085Mercuric ChlorideCatalystHCID 702EthanolSolvent

Procedure

A suspension of 100 g (0.273M) of 5-ethyl-4,5-dihydro-4-hydroxy-9,10-dimethoxy-2-methyl-4-n-propyl-dibenz[cd,f]indole in 2000 ml ethanol is added with stirring to a suspension of 322 g (4.928M) of zinc dust and 74.3 g (0.273M) of mercury(II) chloride in 2000 ml distilled water. The reaction mixture is refluxed, 450 ml of 18% hydrochloric acid are added dropwise over a period of 15 minutes and the mixture is refluxed overnight with stirring. The mixture is then cooled to room temperature, filtered and the zinc amalgam is washed with 500 ml methylene chloride. The filtrate is made alkaline with 1 liter of concentrated NH4OH and extracted three times with methylene chloride (700 ml each time). The combined organic phases are washed with water, dried and evaporated. The resultant oil is chromatographed on silica gel using methylene chloride with 2% methanol to give the title compound as an oil.

Workup

  1. additionis added
  2. distillationdistilled water
  3. temperatureThe reaction mixture is refluxed
  4. addition450 ml of 18% hydrochloric acid are added dropwise over a period of 15 minutes
  5. temperaturethe mixture is refluxed overnight
  6. filtrationfiltered
  7. washthe zinc amalgam is washed with 500 ml methylene chloride
  8. extractionextracted three times with methylene chloride (700 ml each time)
  9. washThe combined organic phases are washed with water
  10. customdried
  11. customevaporated
  12. customThe resultant oil is chromatographed on silica gel

Sources & evidence

ORD record
ord-bffd74ca52984c9f81f0846317d04f99
Source dataset
uspto-grants-1986_07
Patent number
US04602032

Reaction notes

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