Nitric Acid → 1-Methyl-7-nitro-3,4-dihydroisoquinoline

HRID 481780Notes

Reaction equation

HRID 481780 reaction equation
[CH3:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5][CH2:4][N:3]=1.[OH-].[Na+].[N+:14]([O-])([OH:16])=[O:15]>>[CH3:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([N+:14]([O-:16])=[O:15])[CH:10]=2)[CH2:5][CH2:4][N:3]=1

Participants

4

Reactant 3

HCID 944Nitric Acid2×HCID 14798Sodium HydroxideHCID 2315021-Methyl-3,4-dihydroisoquinoline

Product 1

HCID 109322281-Methyl-7-nitro-3,4-dihydroisoquinoline

Procedure

1.0 g of 1-methyl-3,4-dihydroisoquinoline was dissolved in 7.0 ml of conc. nitric acid at 0° C., and 14.0 ml of fuming nitric acid was added dropwise to the solution. The solution was stirred for one hour at the same temperature, and overnight at room temperature. The reaction mixture was poured into ice, neutralized with aqueous solution of sodium hydroxide, and extracted with ethyl acetate. The organic layer was washed with saturated aqueous solution of sodium chloride, and dried with anhydrous sodium sulfate. The desiccant was separated by filtration, and the filtrate was purified by silica gel column chromatography to obtain 1.08 g of 1-methyl-7-nitro-3,4-dihydroisoquinoline, which was white crystal (yield: 82%).

Workup

  1. additionThe reaction mixture was poured into ice
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with saturated aqueous solution of sodium chloride
  4. dry with materialdried 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-e24f2e9a41da499cbe6e9b9bc8c23963
Source dataset
uspto-grants-1998_08
Patent number
US05789595

Reaction notes

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