Nitric Acid → HCID 22750105, compound

HRID 2164045Notes

Reaction equation

HRID 2164045 reaction equation
[CH2:1]([O:3][C:4]1[C:13]2[CH:12]=[CH:11][CH:10]=[C:9]3[N:14]4[C:18]([C:19](=[O:20])[C:7]([C:8]=23)=[CH:6][N:5]=1)=[CH:17][CH:16]=[CH:15]4)[CH3:2].O.[N+:22]([O-])([OH:24])=[O:23]>>[CH2:1]([O:3][C:4]1[C:13]2[CH:12]=[CH:11][CH:10]=[C:9]3[N:14]4[C:18]([C:19](=[O:20])[C:7]([C:8]=23)=[CH:6][N:5]=1)=[CH:17][CH:16]=[C:15]4[N+:22]([O-:24])=[O:23])[CH3:2]

Participants

4

Reactant 3

HCID 944Nitric Acid3×HCID 962WaterHCID 22750102HCID 22750102, compound

Product 1

HCID 22750105HCID 22750105, compound

Procedure

A mixture (150.4 cc) of equal volumes of about 50% by weight nitric acid (density 1.33) and about 97% by weight nitric acid (density 1.52) is added dropwise to a suspension, stirred and maintained between 5° and 10° C., of 4-ethoxy-7-oxo-7H-indolizino[7,6,5-de]isoquinoline (30 g) in nitric acid (density 1.33; l34 cc). The addition takes 15 minutes. The mixture is stirred for a further 15 minutes, whilst allowing the red solution to return to ambient temperature. This solution is poured into water (1.7 liter) and the orange solid which precipitates is filtered off. The residue is washed with water (5 × 50 cc) and then dried under reduced pressure (1 mm Hg) at 50° C. Crude 4-ethoxy-10-nitro-7-oxo-7H-indolizino[7,6,5-de]isoquinoline (31 g) is thus obtained. After recrystallisation from acetonitrile, the pure product melts at 192° C.

Workup

  1. additionThe addition
  2. stirringThe mixture is stirred for a further 15 minutes
  3. customto return to ambient temperature
  4. customthe orange solid which precipitates
  5. filtrationis filtered off
  6. washThe residue is washed with water (5 × 50 cc)
  7. customdried under reduced pressure (1 mm Hg) at 50° C

Sources & evidence

ORD record
ord-e69b911553f74d85bf68cd687136869a
Source dataset
uspto-grants-1979_01
Patent number
US04137315

Reaction notes

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