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

HRID 1173129Notes

Reaction equation

HRID 1173129 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

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

Workup

  1. temperatureby heating
  2. filtrationThe catalyst was filtered off
  3. washwashed with ethanol
  4. customthe filtrate was partially evaporated
  5. extractionAfter extracting with 1N hydrochloric acid
  6. extractionextracted with ethyl acetate
  7. washThe extract was washed with brine
  8. dry with materialdried over anhydrous magnesium sulfate anhydride
  9. customThe solvent was evaporated

Sources & evidence

ORD record
ord-fcfe666d5bc0439eb79fc1e8b0f2baf6
Source dataset
uspto-grants-2010_11
Patent number
US07834049B2

Reaction notes

Loading…