HCID 18361973, compound → HCID 18361907, compound

HRID 382819Notes

Reaction equation

HRID 382819 reaction equation
[CH3:1][C:2]1[C:7]2[C:8](=[O:24])[CH2:9][CH:10]3[CH:15]([C:6]=2[CH:5]=[C:4]([CH3:25])[CH:3]=1)[CH2:14][N:13]([C:16](OC[C:20](Cl)([Cl:22])[Cl:21])=[O:17])[CH2:12][CH2:11]3>C(O)(=O)C.[Zn]>[CH2:20]([Cl:22])[Cl:21].[CH3:16][OH:17].[NH4+:13].[OH-:17].[CH3:1][C:2]1[C:7]2[C:8](=[O:24])[CH2:9][CH:10]3[CH:15]([C:6]=2[CH:5]=[C:4]([CH3:25])[CH:3]=1)[CH2:14][NH:13][CH2:12][CH2:11]3

Participants

5

Reactant 1

HCID 18361973HCID 18361973, compound

Product 2

HCID 18361907HCID 18361907, compoundYield 166.5%HCID 21896990Dichloromethane methanol ammonium hydroxide

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

a 2.2) 250 mg of Zn powder were added to a solution of 890 mg (2.2 mmol) of 2,2,2-trichloroethyl 7,9-dimethyl-6-oxo-3,4,4a,5, 6,10b-hexahydro-1H-benzo[h]isoquinoline-2-carboxylate in 10 ml of glacial acetic acid and the mixture was stirred at room temperature for 16 hrs. The solution was filtered and adjusted to pH 10 with 28% NaOH. The aqueous phase was extracted twice with the 30 ml of methylene chloride, dried (Na2SO4), filtered and evaporated. Chromatography of the residue (silica gel, methylene chloride/methanol/NH4OH 200:10:1) yielded 420 mg (83%) of 7,9-dimethyl-1,3,4,4a,5,10b-hexahydro-2H-benzo[h]isoquinolin-6-one as a colorless oil.

Workup

  1. filtrationThe solution was filtered
  2. extractionThe aqueous phase was extracted twice with the 30 ml of methylene chloride
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-71ca317a18d54e9682b2c58f704e4c24
Source dataset
uspto-grants-2001_10
Patent number
US06310208B1

Reaction notes

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