Nitric Acid → HCID 14251393, compound

HRID 268158Notes

Reaction equation

HRID 268158 reaction equation
[C:1]([CH2:3][CH2:4][N:5]1[C:17]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[C:11]2[C:6]1=[CH:7][CH:8]=[CH:9][CH:10]=2)#[N:2].[N+:18]([O-])([OH:20])=[O:19]>C(O)(=O)C>[C:1]([CH2:3][CH2:4][N:5]1[C:17]2[CH:16]=[CH:15][C:14]([N+:18]([O-:20])=[O:19])=[CH:13][C:12]=2[C:11]2[C:6]1=[CH:7][CH:8]=[CH:9][CH:10]=2)#[N:2]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 2193009H-Carbazole-9-propanenitrile

Product 1

HCID 14251393HCID 14251393, compoundYield 79.9%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Conditions

Temperature
80 °C

Procedure

17,9 g (0.08 mol) of the 9-(β-cyanoethyl)-carbazole thus obtained were suspended in 108 ml glacial acetic acid in a three-necked flask equipped with a stirrer, condenser, thermometer and dropping funnel and a mixture of 13.5 ml glacial acetic acid and 6.75 ml 65% nitric acid were added dropwise, while stirring, at 80°C, the nitrile thereby going into solution. The reaction mixture was further stirred for 15 minutes at 80°C, cooled and thereafter added dropwise into 200 ml ice water. The precipitated nitro compound was filtered off with suction, washed with a little water and the crude product recyrstallized from acetone. There were obtained 17.2 g (79.9% of theory) 9-(β-cyanoethyl)-3-nitrocarbazole in the form of yellow-green crystals with a melting point of 225°C.

Workup

  1. customequipped with a stirrer, condenser
  2. additionwere added dropwise
  3. stirringThe reaction mixture was further stirred for 15 minutes at 80°C
  4. temperaturecooled
  5. filtrationThe precipitated nitro compound was filtered off with suction
  6. washwashed with a little water

Sources & evidence

ORD record
ord-edcb74f5be0a41b2aacbe0327ce3ee42
Source dataset
uspto-grants-1976_03
Patent number
US03947377

Reaction notes

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