Nitric Acid → 6-Methoxy-7-nitro-3,4-dihydroisoquinolin-1(2H)-one

HRID 1014306Notes

Reaction equation

HRID 1014306 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9](=[O:13])[NH:8][CH2:7][CH2:6]2.[N+:14]([O-])([OH:16])=[O:15]>OS(O)(=O)=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[N+:14]([O-:16])=[O:15])[C:9](=[O:13])[NH:8][CH2:7][CH2:6]2

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 106073926-methoxy-3,4-dihydroisoquinolin-1(2H)-one

Product 1

HCID 594417296-Methoxy-7-nitro-3,4-dihydroisoquinolin-1(2H)-oneYield 75.9%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
-20 °C

Procedure

To a solution of 6-(methyloxy)-3,4-dihydro-1(2H)-isoquinolinone (3.4 g, 17.8 mmol) in H2SO4 (45 mL) at −20° C. was added HNO3 (1.58 mL, 21.3 mmol) dropwise. The mixture was allowed to stir for 3 h at −20° C. The mixture was poured into ice water and the aqueous layer was extracted with dichloromethane. The combined organic layers were concentrated under reduced pressure to give 6-(methyloxy)-7-nitro-3,4-dihydro-1(2H)-isoquinolinone (3.0 g, 71%). 1H NMR (CDCl3) δ 8.55 (1H), 6.88 (1H), 6.2 (1H), 4.0 (3H), 3.6 (2H), 3.05 (2H).

Workup

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

Sources & evidence

ORD record
ord-7c03e89b4a4a4164bd58a8a16d000b2a
Source dataset
uspto-grants-2011_07
Patent number
US07981903B2

Reaction notes

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