Nitric Acid → HCID 12911926, compound

HRID 2058493Notes

Reaction equation

HRID 2058493 reaction equation
[O:1]=[C:2]1[C:7]2[CH:8]=[CH:9][CH:10]=[C:11]3[CH:12]4[CH:17]([N:5]([C:6]=23)[CH:4]=[C:3]1[C:18]([OH:20])=[O:19])[CH2:16][CH2:15][CH2:14][CH2:13]4.[N+:21]([O-])([OH:23])=[O:22]>S(=O)(=O)(O)O>[N+:21]([C:8]1[C:7]2[C:2](=[O:1])[C:3]([C:18]([OH:20])=[O:19])=[CH:4][N:5]3[C:6]=2[C:11]([CH:12]2[CH:17]3[CH2:16][CH2:15][CH2:14][CH2:13]2)=[CH:10][CH:9]=1)([O-:23])=[O:22]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 12911915HCID 12911915, compound

Product 1

HCID 12911926HCID 12911926, compound

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Procedure

6 g of 7a,8,9,10,11,11a-hexahydro-4-oxo-4H-pyrido[3,2,1-jk]carbazole-5-carboxylic acid was dissolved in 35 ml of concentrated sulfuric acid and stirred while cooling with ice, followed by dropwise addition of a mixture of 4.3 ml of concentrated nitric acid having a specific gravity of 1.42 and 15 ml of the concentrated sulfuric acid. After completion of the addition, the resulting mixture was stirred for 1 hour at room temperature and poured into 200 g of ice to precipitate yellow crystals. Recrystallization from dimethylformamide-water gave 7 g of 3-nitro-7a,8,9,10,11,11a-hexahydro-4-oxo-4H-pyrido[3,2,1-jk]carbazole-5-carboxylic acid having a melting point of 251°-253° C.

Workup

  1. temperaturewhile cooling with ice
  2. additionAfter completion of the addition
  3. stirringthe resulting mixture was stirred for 1 hour at room temperature
  4. customto precipitate yellow crystals
  5. customRecrystallization from dimethylformamide-water

Sources & evidence

ORD record
ord-30d43c634aaa4c5fbae803e487385a28
Source dataset
uspto-grants-1982_03
Patent number
US04317820

Reaction notes

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