Nitric Acid → HCID 21394685, compound

HRID 1283413Notes

Reaction equation

HRID 1283413 reaction equation
CN(C)CCN1C2C=CC=CC=2C2C1=CC=CC=2.[N+]([O-])(O)=O.[CH3:23][N:24]([CH3:43])[CH2:25][CH2:26][N:27]1[C:39]2[CH:38]=[CH:37][C:36]([N+:40]([O-])=O)=[CH:35][C:34]=2[C:33]2[C:28]1=[CH:29][CH:30]=[CH:31][CH:32]=2>C(O)(=O)C>[CH3:23][N:24]([CH3:43])[CH2:25][CH2:26][N:27]1[C:39]2[CH:38]=[CH:37][C:36]([NH2:40])=[CH:35][C:34]=2[C:33]2[C:28]1=[CH:29][CH:30]=[CH:31][CH:32]=2

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 23860Carbazole, 9-(2-(dimethylamino)ethyl)-HCID 432702N,N-dimethyl-2-(3-nitrocarbazol-9-yl)ethanamine

Product 1

HCID 21394685HCID 21394685, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

23.7 g. (0.1 mol) 9-(β-dimethylaminoethyl)-carbazole (prepared in the manner described by O. Eisleb, Ber. dtsch. chem. Ges., 74, 1433/1941) in 100 ml. glacial acetic acid were placed in a 500 ml. three-necked flask equipped with a stirrer, thermometer and dropping funnel and placed in an ice-bath. A solution of 8.28 ml. (0.2 mol) anhydrous nitric acid in 50 ml. glacial acetic acid was added dropwise thereto at 15° - 20°C. The reaction mixture was further stirred for an hour at 20° - 25°C. and then poured into 500 ml. ice-water. The precipitated green crystals were filtered off with suction, well washed with water and dried at 80°C. in a drying cabinet. There were obtained 32.4 g. (94% of theory) 9-(β-dimethylaminoethyl)-3-nitrocarbazole which melted, with decomposition, at 190°C.

Workup

  1. customthree-necked flask equipped with a stirrer
  2. customplaced in an ice-bath
  3. customat 15° - 20°C
  4. additionpoured into 500 ml
  5. filtrationThe precipitated green crystals were filtered off with suction
  6. washwell washed with water
  7. customdried at 80°C. in a drying cabinet
  8. customThere were obtained 32.4 g
  9. custommelted, with decomposition, at 190°C.

Sources & evidence

ORD record
ord-43009954308748c58a74b40efe4a1cb7
Source dataset
uspto-grants-1976_08
Patent number
US03975398

Reaction notes

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