Nitric Acid → 3,4-Dihydro-9-methylamino-7-nitroacridin-1(2H)-one

HRID 1904697Notes

Reaction equation

HRID 1904697 reaction equation
[CH3:1][NH:2][C:3]1[C:4]2[C:9]([N:10]=[C:11]3[C:16]=1[C:15](=[O:17])[CH2:14][CH2:13][CH2:12]3)=[CH:8][CH:7]=[CH:6][CH:5]=2.[N+:18]([O-])([OH:20])=[O:19].[OH-].[Na+]>OS(O)(=O)=O>[CH3:1][NH:2][C:3]1[C:4]2[C:9]([N:10]=[C:11]3[C:16]=1[C:15](=[O:17])[CH2:14][CH2:13][CH2:12]3)=[CH:8][CH:7]=[C:6]([N+:18]([O-:20])=[O:19])[CH:5]=2

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 14798Sodium HydroxideHCID 13756050HCID 13756050, compound

Product 1

HCID 137560523,4-Dihydro-9-methylamino-7-nitroacridin-1(2H)-oneYield 47%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

In 100 ml of concentrated H2SO4 at 0° C. was added 4.83 g of 3,4-dihydro-9-(methylamino)acridin-1(2H)-one. While maintaining the reaction at 0° C., 1.92 ml (1 eq) of concentrated HNO3 (70 wt %) was added dropwise over 10 minutes. Since the reaction appeared complete after the addition based on thin layer chromatography, the reaction mixture was poured into ice and neutralized with 50% NaOH. At the basic point a precipitate formed. This was filtered and chromatographed on silica gel (EtOAc) and the product was recrystallized from dichloromethane/hexanes to yield 2.75 g (47%) of a solid, melting point 208° C.

Workup

  1. temperatureWhile maintaining
  2. customthe reaction at 0° C.
  3. additionafter the addition
  4. customAt the basic point a precipitate formed
  5. filtrationThis was filtered
  6. customchromatographed on silica gel (EtOAc)
  7. customthe product was recrystallized from dichloromethane/hexanes

Sources & evidence

ORD record
ord-24cf0cf3f86c4f5ea6ee1c53fff85185
Source dataset
uspto-grants-1989_06
Patent number
US04839364

Reaction notes

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