Hydrochloric Acid → HCID 19067179, compound

HRID 481784Notes

Reaction equation

HRID 481784 reaction equation
C([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])C.[OH-].[Na+].Cl>C(O)C>[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)([OH:5])=[O:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 190671552-(2-(Ethoxycarbonyl)ethyl)-7-nitro-1,2,3,4-tetrahydroisoquinoline

Product 1

HCID 19067179HCID 19067179, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3.51 g of 2-(2-(ethoxycarbonyl)ethyl)-7-nitro-1,2,3,4-tetrahydroisoquinoline was dissolved in 100 ml of ethanol, and 13.0 ml of 2N aqueous solution of sodium hydroxide was added to the solution. The solution was stirred overnight at room temperature. Dilute hydrochloric acid was added dropwise to the resulting solution to acidify the solution, and the solution was concentrated under reduced pressure, and dissolved in anhydrous ethanol. The insoluble content was separated by filtration, and the solvent was distilled off to obtain crude crystals of 2-(2-carboxyethyl)-7-nitro-1,2,3,4-tetrahydroisoquinoline. The crystals, with no further purification, were dissolved in 20 ml of DMF, and the solution was neutralized by adding 1.8 ml of triethylamine. To this solution were added 1.93 g of benzylalcohol, 3.42 g of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide, and 1.93 g of 1-hydroxybenzotriazol, and the solution was stirred overnight at room temperature. The resulting solution was extracted with ethyl acetate, washed with water, saturated aqueous solution of sodium bicarbonate, and saturated aqueous solution of sodium chloride, and dried with anhydrous sodium sulfate. After separating the desiccant by filtration, the filtrate was purified by silica gel column chromatography to obtain 1.60 g of 2-(2-benzyloxycarbonylethyl)-7-nitro-1,2,3,4-tetrahydroisoquinoline, which was an oily product (yield: 49%).

Workup

  1. concentrationthe solution was concentrated under reduced pressure
  2. dissolutiondissolved in anhydrous ethanol
  3. customThe insoluble content was separated by filtration
  4. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-929271dc1dea49fea778c09ca1cc56b8
Source dataset
uspto-grants-1998_08
Patent number
US05789595

Reaction notes

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