Triethylamine → 2-(2-(Ethoxycarbonyl)ethyl)-7-nitro-1,2,3,4-tetrahydroisoquinoline

HRID 481770Notes

Reaction equation

HRID 481770 reaction equation
Cl.[N+:2]([C:5]1[CH:14]=[C:13]2[C:8]([CH2:9][CH2:10][NH:11][CH2:12]2)=[CH:7][CH:6]=1)([O-:4])=[O:3].C(N(CC)CC)C.[C:22]([O:26][CH2:27][CH3:28])(=[O:25])[CH:23]=[CH2:24]>C(O)C>[CH2:27]([O:26][C:22]([CH2:23][CH2:24][N:11]1[CH2:10][CH2:9][C:8]2[C:13](=[CH:14][C:5]([N+:2]([O-:4])=[O:3])=[CH:6][CH:7]=2)[CH2:12]1)=[O:25])[CH3:28]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 8821Ethyl AcrylateHCID 135216707-Nitro-1,2,3,4-tetrahydroisoquinoline hydrochloride

Product 1

HCID 190671552-(2-(Ethoxycarbonyl)ethyl)-7-nitro-1,2,3,4-tetrahydroisoquinoline

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 125 ml of suspension in ethanol of 136 g of 7-nitro-1,2,3,4-tetrahydroisoquinoline hydrochloride was added 98 ml of triethylamine and 83 ml of ethyl acrylate, and the solution was heated and stirred overnight under reflux. The solution was concentrated under reduced pressure, and the residue was extracted with ethyl acetate, washed with water, and dried with anhydrous sodium sulfate. After separating the desiccant by filtration, the filtrate was concentrated under reduced pressure to obtain 2-(2-(ethoxycarbonyl)ethyl)-7-nitro-1,2,3,4-tetrahydroisoquinoline. The thus obtained 2-(2-(ethoxycarbonyl)ethyl)-7-nitro-1,2,3,4-tetrahydroisoquinoline was dissolved in 1,000 ml of ethanol, and a catalytic amount of 10% palladium-carbon was added to the solution. The solution was stirred overnight under hydrogen atmosphere. The catalyst was separated by filtration, and the filtrate was concentrated under reduced pressure to obtain 7-amino-2-(2-(ethoxycarbonyl)ethyl)-1,2,3,4-tetrahydroisoquinoline, which was a solid.

Workup

  1. temperaturethe solution was heated
  2. temperatureunder reflux
  3. concentrationThe solution was concentrated under reduced pressure
  4. extractionthe residue was extracted with ethyl acetate
  5. washwashed with water
  6. dry with materialdried with anhydrous sodium sulfate
  7. customAfter separating the desiccant
  8. filtrationby filtration
  9. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-8c2d0e0002fb4508821a7428bf6bec93
Source dataset
uspto-grants-1998_08
Patent number
US05789595

Reaction notes

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