Nitric Acid → 2,4,4-Trimethyl-7-nitroisoquinoline-1,3(2H,4H)-dione

HRID 650945Notes

Reaction equation

[CH3:1][N:2]1[C:11](=[O:12])[C:10]([CH3:14])([CH3:13])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]1=[O:15].[N+:16]([O-])([OH:18])=[O:17]>S(=O)(=O)(O)O>[N+:16]([C:6]1[CH:5]=[C:4]2[C:9]([C:10]([CH3:13])([CH3:14])[C:11](=[O:12])[N:2]([CH3:1])[C:3]2=[O:15])=[CH:8][CH:7]=1)([O-:18])=[O:17]

Participants

Conditions

Temperature: 25 °C

Procedure

2,4,4-Trimethyl-4H-isoquinoline-1,3-dione (5 g, 24.6 mmol) [prepared according to H. Takechi et al., Synthesis. 1992, 778] was dissolved in concentrated sulfuric acid (50 ml) at 0° C. Fuming nitric acid (2.5 ml) was added dropwise over 5 min and the reaction warmed to 25° C. After stirring for 30 min at 25° C. the reaction mixture was poured into ice water (100 ml) and the organics extracted into dichloromethane (3×50 ml). The combined organic extracts were dried over magnesium sulfate and evaporated in vacuo to give the title compound (5.31 g, 86%).

Workup

extractionthe organics extracted into dichloromethane (3×50 ml)
dry with materialThe combined organic extracts were dried over magnesium sulfate
customevaporated in vacuo

Sources & evidence

ORD record: ord-bcd3a33c1a204450a030968a4e9e8897
Source dataset: uspto-grants-2001_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06277861B1

Reaction notes

Loading…