Nitric Acid → HCID 59442114, compound

HRID 1014303Notes

Reaction equation

HRID 1014303 reaction equation
[CH3:1][N:2]1[CH2:11][CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:12][CH3:13])[CH:8]=2)[C:3]1=[O:14].[N+:15]([O-])([OH:17])=[O:16]>OS(O)(=O)=O.O>[CH3:1][N:2]1[CH2:11][CH2:10][C:9]2[C:4](=[CH:5][C:6]([N+:15]([O-:17])=[O:16])=[C:7]([O:12][CH3:13])[CH:8]=2)[C:3]1=[O:14]

Participants

5

Reactant 2

HCID 944Nitric AcidHCID 25233016HCID 25233016, compound

Product 1

HCID 59442114HCID 59442114, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1118Sulfuric AcidSolvent

Conditions

Temperature
-20 °C

Procedure

To a solution of 2-methyl-6-(methyloxy)-3,4-dihydro-1(2H)-isoquinolinone (5 g, 26.17 mmol) in H2SO4(2.17 mL) was added HNO3 (1.95 g, 31.4 mmol) dropwise at −20° C. The mixture was stirred for 2 h at −20° C. The reaction was diluted with water and the aqueous layer was extracted with dichloromethane. The combined organic layer was concentrated under reduced pressure to afford 2-methyl-6-(methyloxy)-7-nitro-3,4-dihydro-1(2H)-isoquinolinone (4.7 g, 75.8%).

Workup

  1. extractionthe aqueous layer was extracted with dichloromethane
  2. concentrationThe combined organic layer was concentrated under reduced pressure

Sources & evidence

ORD record
ord-12cc5fe0e2d043969ab9131888c0b8af
Source dataset
uspto-grants-2011_07
Patent number
US07981903B2

Reaction notes

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