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

HRID 481766Notes

Reaction equation

HRID 481766 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[CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23].[I-].[K+]>C(O)C>[CH2:25]([O:24][C:22]([CH2:21][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 7748Ethyl bromoacetateHCID 516892Sodium BicarbonateHCID 135216707-Nitro-1,2,3,4-tetrahydroisoquinoline hydrochloride

Product 1

HCID 106116392-(Ethoxycarbonylmethyl)-7-nitro-1,2,3,4-tetrahydroisoquinolineYield 59.6%

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 bromoacetate, 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 the water and saturated aqueous solution of sodium chloride, and then dried with anhydrous sodium sulfate. After separating the desiccant by filtration, the filtrate was purified by silica gel column chromatography to obtain 1.1 g of 2-(ethoxycarbonylmethyl)-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 the 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 filtrate was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-e50070ab9dcd486382ddace217eb88d7
Source dataset
uspto-grants-1998_08
Patent number
US05789595

Reaction notes

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