Ethanol → 2-(2-(Isopropyloxycarbonyl)ethyl)-7-nitro-1,2,3,4-tetrahydroisoquinoline

HRID 481786Notes

Reaction equation

HRID 481786 reaction equation
[CH2:1]([O:3][C:4]([CH2:6][CH2:7][N:8]1[CH2:17][CH2:16][C:15]2[C:10](=[CH:11][C:12]([N+:18]([O-:20])=[O:19])=[CH:13][CH:14]=2)[CH2:9]1)=[O:5])[CH3:2].[OH-].[Na+].[CH2:23](O)C>>[CH:1]([O:3][C:4]([CH2:6][CH2:7][N:8]1[CH2:17][CH2:16][C:15]2[C:10](=[CH:11][C:12]([N+:18]([O-:20])=[O:19])=[CH:13][CH:14]=2)[CH2:9]1)=[O:5])([CH3:23])[CH3:2]

Participants

4

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 190671552-(2-(Ethoxycarbonyl)ethyl)-7-nitro-1,2,3,4-tetrahydroisoquinoline

Product 1

HCID 190672012-(2-(Isopropyloxycarbonyl)ethyl)-7-nitro-1,2,3,4-tetrahydroisoquinolineYield 74%

Procedure

To the solution (60 ml) in ethanol of 2.04 g of 2-(2-(ethoxycarbonyl)ethyl)-7-nitro-1,2,3,4-tetrahydroisoquinoline obtained in Example 2 was added 3.75 ml of 2N aqueous solution of sodium hydroxide, and the solution was stirred at room temperature for 14 hours. The solution was concentrated under reduced pressure, and to the residue were added 300 ml of isopropylalcohol and 0.60 ml of sulfuric acid. The solution was heated under reflux for 20 hours, and concentrated under reduced pressure. After adding saturated aqueous solution of sodium bicarbonate to the residue, the solution was extracted with ethyl acetate, washed with water, dried with anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to obtain 1.58 g of 2-(2-(isopropyloxycarbonyl)ethyl)-7-nitro-1,2,3,4-tetrahydroisoquinoline (yield: 74%).

Workup

  1. concentrationThe solution was concentrated under reduced pressure
  2. additionto the residue were added 300 ml of isopropylalcohol and 0.60 ml of sulfuric acid
  3. temperatureThe solution was heated
  4. temperatureunder reflux for 20 hours
  5. concentrationconcentrated under reduced pressure
  6. additionAfter adding saturated aqueous solution of sodium bicarbonate to the residue
  7. extractionthe solution was extracted with ethyl acetate
  8. washwashed with water
  9. dry with materialdried with anhydrous sodium sulfate
  10. concentrationconcentrated under reduced pressure
  11. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-ea3f93a10fbf467c93ca105e0d5870bd
Source dataset
uspto-grants-1998_08
Patent number
US05789595

Reaction notes

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