6-Ethoxycarbonylamino-1-methyl-3,4-dihydroisoquinoline → 6-Ethoxycarbonylamino-1-methylisoquinoline

HRID 1005686Notes

Reaction equation

HRID 1005686 reaction equation
[CH2:1]([O:3][C:4]([NH:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[C:13]([CH3:17])=[N:12][CH2:11][CH2:10]2)=[O:5])[CH3:2]>[C].[Pd].CC1C=CC(C(C)C)=CC=1>[CH2:1]([O:3][C:4]([NH:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[C:13]([CH3:17])=[N:12][CH:11]=[CH:10]2)=[O:5])[CH3:2]

Participants

4

Reactant 1

HCID 226741196-Ethoxycarbonylamino-1-methyl-3,4-dihydroisoquinoline

Product 1

HCID 226741466-Ethoxycarbonylamino-1-methylisoquinolineYield 69%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 7463P-CymeneSolvent

Conditions

Temperature
195 °C

Procedure

To 6-ethoxycarbonylamino-1-methyl-3,4-dihydroisoquinoline were added p-cymene (100 ml) and palladium-carbon (0.9 g), followed by heating under stirring at 195° C. in nitrogen atmosphere for 1 hour. After filtering off the catalyst, the reaction mixture was washed with ethanol and a part of the filtrate was evaporated. The residue was extracted with 1N hydrochloric acid, and then basified with potassium carbonate, followed by extracting with ethyl acetate. The extract was washed with brine, dried over anhydrous magnesium sulfate and the solvent was evaporated, to give the title compound (0.629 g, 69%, 2 steps) as pale yellow crystals.

Workup

  1. temperatureby heating
  2. filtrationAfter filtering off the catalyst
  3. washthe reaction mixture was washed with ethanol
  4. customa part of the filtrate was evaporated
  5. extractionThe residue was extracted with 1N hydrochloric acid
  6. extractionby extracting with ethyl acetate
  7. washThe extract was washed with brine
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customthe solvent was evaporated

Sources & evidence

ORD record
ord-cc620b2e56c34eaf9a16db20048571e6
Source dataset
uspto-grants-2004_09
Patent number
US06787534B2

Reaction notes

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