Sodium Hydroxide → 1,3-Dimethyl-5-nitroisoquinoline

HRID 490293Notes

Reaction equation

HRID 490293 reaction equation
[CH3:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[C:4]([CH3:12])[N:3]=1.[N+:13]([O-])([O-:15])=[O:14].[K+].[OH-].[Na+]>S(=O)(=O)(O)O>[CH3:1][C:2]1[C:11]2[C:6](=[C:7]([N+:13]([O-:15])=[O:14])[CH:8]=[CH:9][CH:10]=2)[CH:5]=[C:4]([CH3:12])[N:3]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 24434Potassium NitrateHCID 744021,3-Dimethylisoquinoline

Product 1

HCID 574567801,3-Dimethyl-5-nitroisoquinoline

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Procedure

1,3-Dimethylisoquinoline [(Chem. Lett., 1983, p.791), 2.39 g, 15.20 mM], in conc. sulfuric acid, (15 ml), was cooled to below 4° C. A solution of potassium nitrate (1.69 g, 16.72 mM) in conc. sulfuric acid was added dropwise, maintaining the temperature below 4° C. After complete addition the solution was stirred at this temperature for a further 2 h. then warmed to room temperature for 1 h. The reaction mixture was poured into ice water and the solution basified with sodium hydroxide and extracted with DCM. The extract was washed with brine, dried and concentrated to a yellow solid. Purification by silica gel chromatography afforded the title compound as a yellow crystalline solid.

Workup

  1. temperaturemaintaining the temperature below 4° C
  2. additionAfter complete addition the solution
  3. extractionextracted with DCM
  4. washThe extract was washed with brine
  5. customdried
  6. concentrationconcentrated to a yellow solid
  7. customPurification by silica gel chromatography

Sources & evidence

ORD record
ord-fc3cac47f3c24ed2b2dc519c1f893c6d
Source dataset
uspto-grants-2009_05
Patent number
US07528151B2

Reaction notes

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