Nitric Acid → HCID 620863, compound
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]=2Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To 100 ml of cold H2SO4 was added 5.00 g of 9-amino-3,4-dihydroacridin-1(2H)-one. The mechanically stirred solution was cooled to 0° C. and 2.1 ml (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
- additionafter the addition
- additionThe reaction mixture was poured
- custominto excess crushed ice
- additionMore ice was added during the neutralization
- temperaturecool
- filtrationThe resulting precipitate was filtered
- customchromatographed over silica gel (ETOAc)
- additionThe fractions containing the product
- customwere evaporated to a solid which
- customwas triturated with pentane
Sources & evidence
- ORD record
- ord-6487a52f5f634e2daad650ed69f2d824
- Source dataset
- uspto-grants-1987_09
- Patent number
- US04695573
Reaction notes
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