Potassium Nitrate → 7-Nitro-9-oxo-9,10-dihydroacridine-4-carboxylic acid

HRID 280719Notes

Reaction equation

HRID 280719 reaction equation
[C:1]([C:4]1[C:17]2[NH:16][C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9](=[O:18])[C:8]=2[CH:7]=[CH:6][CH:5]=1)([OH:3])=[O:2].[N+:19]([O-])([O-:21])=[O:20].[K+]>OS(O)(=O)=O>[N+:19]([C:12]1[CH:11]=[C:10]2[C:15]([NH:16][C:17]3[C:4]([C:1]([OH:3])=[O:2])=[CH:5][CH:6]=[CH:7][C:8]=3[C:9]2=[O:18])=[CH:14][CH:13]=1)([O-:21])=[O:20]

Participants

4

Reactant 2

HCID 24434Potassium NitrateHCID 35607584-Carboxy-9-acridanone

Product 1

HCID 5420897-Nitro-9-oxo-9,10-dihydroacridine-4-carboxylic acidYield 65%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
20 °C

Procedure

A stirred solution of 4-carboxyacridanone (10.0 g) in c.H2SO4 (50 ml) was treated portionwise at below 5° C. with powdered KNO3 (4.6 g), then stirred for 30 min at 20° C. and poured into ice water. The precipitate was collected, washed, dried and crystallized from DMF/MeOH and then DMF to give pure product of m.p. about 375° C. (65% yield).

Workup

  1. customThe precipitate was collected
  2. washwashed
  3. customdried
  4. customcrystallized from DMF/MeOH
  5. customDMF to give pure product of m.p. about 375° C. (65% yield)

Sources & evidence

ORD record
ord-8948984e25fb4a5ca049c21f277aa505
Source dataset
uspto-grants-1986_05
Patent number
US04590277

Reaction notes

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