Isoquinoline → 5-Nitroisoquinoline

HRID 1520233Notes

Reaction equation

HRID 1520233 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][N:2]=1.[N+:11]([O-])([O-:13])=[O:12].[K+].C(OCC)(=O)C.[NH4+].[OH-]>OS(O)(=O)=O.O>[N+:11]([C:6]1[CH:7]=[CH:8][CH:9]=[C:10]2[C:5]=1[CH:4]=[CH:3][N:2]=[CH:1]2)([O-:13])=[O:12]

Participants

7

Reactant 4

HCID 8405IsoquinolineHCID 8857Ethyl AcetateHCID 14923Ammonium HydroxideHCID 24434Potassium Nitrate

Product 1

HCID 690855-NitroisoquinolineYield 98.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1118Sulfuric AcidSolvent

Procedure

To a solution of isoquinoline (120 g, 0.929 mol) in H2SO4 (1 L)was added KNO3 (112.6 g, 1.115 mol) at −15° C. (portionwise). The mixture was stirred at room temperature for 2 hours. TLC (petroleum ether:ethyl acetate=2:1) showed the reaction was complete. The mixture was added to water (3 L) at 0° C. The mixture was adjusted to pH 8 by the addition of NH4OH and filtered. The filter cake was washed with methyl tertbutyl ether (1 L×2) and concentrated in vacuo to give 5-nitro-isoquinoline (160 g, 94%) as a yellow solid.

Workup

  1. filtrationfiltered
  2. washThe filter cake was washed with methyl tertbutyl ether (1 L×2)
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0a0084d44f6e4a8fb7aac388873f2fd6
Source dataset
uspto-grants-2015_07
Patent number
US09073905B2

Reaction notes

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