Nitric Acid → HCID 620863, compound

HRID 1763006Notes

Reaction equation

HRID 1763006 reaction equation
[NH2:1][C:2]1[C:3]2[C:8]([N:9]=[C:10]3[C:15]=1[C:14](=[O:16])[CH2:13][CH2:12][CH2:11]3)=[CH:7][CH:6]=[CH:5][CH:4]=2.[N+:17]([O-])([OH:19])=[O:18].[OH-].[Na+]>OS(O)(=O)=O>[NH2:1][C:2]1[C:3]2[C:8]([N:9]=[C:10]3[C:15]=1[C:14](=[O:16])[CH2:13][CH2:12][CH2:11]3)=[CH:7][CH:6]=[C:5]([N+:17]([O-:19])=[O:18])[CH:4]=2

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 14798Sodium HydroxideHCID 1843619-amino-3,4-dihydroacridin-1(2H)-one

Product 1

HCID 620863HCID 620863, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
20 °C

Procedure

To 100ml of cold H2SO4 was added 5.00 g of 9-amino-3,4-di-hydroacridin-1(2H)-one. The mechanically stirred solution was cooled to 20° C. and 2.1ml (1 eq) of concentrated HNO3 (70 wt % solution) was added dropwise. Stirring was continued for 15 minutes after the addition, whereupon the reaction was complete. The reaction mixture was poured into excess crushed ice and made basic with a slight excess of 50% NaOH solution. More ice was added during the neutralization to keep the solution cool. The resulting precipitate was filtered and chromatographed over silica gel (EtOAc). The fractions containing the product were evaporated to a solid which was triturated with pentane to yield 4.77 g (79%) of a solid after drying, melting point 254° C. (with decomposition).

Workup

  1. additionafter the addition
  2. additionThe reaction mixture was poured
  3. custominto excess crushed ice
  4. additionMore ice was added during the neutralization
  5. temperaturecool
  6. filtrationThe resulting precipitate was filtered
  7. customchromatographed over silica gel (EtOAc)
  8. additionThe fractions containing the product
  9. customwere evaporated to a solid which
  10. customwas triturated with pentane

Sources & evidence

ORD record
ord-d03b7bf44926463782b87b23c03ed803
Source dataset
uspto-grants-1989_05
Patent number
US04835275

Reaction notes

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