Water → 1-Methyl-7-nitro-1,2,3,4-tetrahydroisoquinoline

HRID 481781Notes

Reaction equation

HRID 481781 reaction equation
[CH3:1][C: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][N:3]=1.[BH4-].[Na+].O>CO>[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

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 109322281-Methyl-7-nitro-3,4-dihydroisoquinoline

Product 1

HCID 215843111-Methyl-7-nitro-1,2,3,4-tetrahydroisoquinolineYield 82.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1.08 g of 1-methyl-7-nitro-3,4-dihydroisoquinoline was dissolved in 10 ml of methanol, and 0.43 g of sodium borohydride was added to the solution at 0° C. The solution was stirred overnight at room temperature, and water was added to the reaction mixture. The mixture was extracted with ethyl acetate, and after washing with 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 1-methyl-7-nitro-1,2,3,4-tetrahydroisoquinoline, which was an oily product (yield: 82%).

Workup

  1. extractionThe mixture was extracted with ethyl acetate
  2. washafter washing with saturated aqueous solution of sodium chloride
  3. dry with materialthe solution was dried with anhydrous sodium sulfate
  4. customThe desiccant was separated by filtration
  5. customthe filtrate was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-a27e714908bf4ba4b1cf51f6fb4b7765
Source dataset
uspto-grants-1998_08
Patent number
US05789595

Reaction notes

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