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

HRID 481782Notes

Reaction equation

HRID 481782 reaction equation
[CH3:1][CH:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([N+:12]([O-:14])=[O:13])[CH:10]=2)[CH2:5][CH2:4][NH:3]1.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:3]1[CH2:4][CH2:5][C:6]2[C:11](=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[CH:8][CH:7]=2)[CH:2]1[CH3:1])=[O:23])[CH3:26]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 79040Ethyl 2-bromopropionateHCID 516892Sodium BicarbonateHCID 215843111-Methyl-7-nitro-1,2,3,4-tetrahydroisoquinoline

Product 1

HCID 190671742-[2-(Ethoxycarbonyl)ethyl]-1-methyl-7-nitro-1,2,3,4-tetrahydroisoquinolineYield 65.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

0.90 g of 1-methyl-7-nitro-1,2,3,4-tetrahydroisoquinoline was dissolved in 20 ml of ethanol, and 1.97 g of sodium bicarbonate, 2.55 g of ethyl bromopropionate, and a catalytic amount of potassium iodide were added to the solution. The solution was heated overnight under ref lux with stirring, and extracted with ethyl acetate. After washing with water and saturated aqueous solution of sodium chloride, the solution was dried with anhydrous sodium sulfate. The desiccant was separated by filtration, and the filtrate was purified by silica gel column chromatography to obtain 0.90 g of 2-[2-(ethoxycarbonyl)ethyl]-1-methyl-7-nitro-1,2,3,4-tetrahydroisoquinoline, which was an oily product (yield: 65%).

Workup

  1. temperatureThe solution was heated overnight under ref lux
  2. extractionextracted with ethyl acetate
  3. washAfter washing with water and saturated aqueous solution of sodium chloride
  4. dry with materialthe solution was dried with anhydrous sodium sulfate
  5. customThe desiccant was separated by filtration
  6. customthe filtrate was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-8a206188ea6741718409527477fd8814
Source dataset
uspto-grants-1998_08
Patent number
US05789595

Reaction notes

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