Nitric Acid → HCID 12911926, compound

HRID 847783Notes

Reaction equation

HRID 847783 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]carbazol-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 and 15 ml of the concentrated sulfuric acid. After completion of the addition, the resulting mixture was stirred for one 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]carbazol-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 one hour at room temperature
  4. customto precipitate yellow crystals
  5. customRecrystallization from dimethylformamide-water

Sources & evidence

ORD record
ord-84f1f75dc0f441f2b9ff27d25c28ed6e
Source dataset
uspto-grants-1981_10
Patent number
US04293694

Reaction notes

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