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

HRID 481768Notes

Reaction equation

HRID 481768 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(=O)([O-])O.[Na+].Br[CH:21]([CH3:27])[C:22]([O:24][CH2:25][CH3:26])=[O:23].[I-].[K+]>C(O)C>[CH2:25]([O:24][C:22]([CH2:21][CH2:27][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:23])[CH3:26]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 79040Ethyl 2-bromopropionateHCID 516892Sodium BicarbonateHCID 135216707-Nitro-1,2,3,4-tetrahydroisoquinoline hydrochloride

Product 1

HCID 190671552-(2-(Ethoxycarbonyl)ethyl)-7-nitro-1,2,3,4-tetrahydroisoquinolineYield 57%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1.5 g of 7-nitro-1,2,3,4-tetrahydroisoquinoline hydrochloride was dissolved in 20 ml of ethanol, and 2.9 g of sodium hydrogencarbonate, 2.3 g of ethyl bromopropionate, and a catalytic amount of potassium iodide were added to the solution. The resulting solution was heated and stirred overnight under reflux. The resulting solution was extracted with ethyl acetate, washed with water and saturated aqueous solution of sodium chloride, and then dried with anhydrous sodium sulfate. After separating the desiccant by filtration, the product was purified by silica gel column chromatography to obtain 1.1 g of 2-(2-(ethoxycarbonyl)ethyl)-7-nitro-1,2,3,4-tetrahydroisoquinoline (yield: 57%, oily product).

Workup

  1. temperatureThe resulting solution was heated
  2. temperatureunder reflux
  3. extractionThe resulting solution was extracted with ethyl acetate
  4. washwashed with water and saturated aqueous solution of sodium chloride
  5. dry with materialdried with anhydrous sodium sulfate
  6. customAfter separating the desiccant
  7. filtrationby filtration
  8. customthe product was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-a4b0d6a07ce54855aa0524b1048221fd
Source dataset
uspto-grants-1998_08
Patent number
US05789595

Reaction notes

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