Nitric Acid → 9-ethyl-3-nitro-9H-carbazole

HRID 1763217

Reaction equation

HRID 1763217 reaction equation
[N+:1]([O-:4])(O)=[O:2].[CH2:5]([N:7]1[C:19]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[C:13]2[C:8]1=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH3:6].O>C(O)(=O)C>[N+:1]([C:11]1[CH:10]=[CH:9][C:8]2[N:7]([CH2:5][CH3:6])[C:19]3[C:14]([C:13]=2[CH:12]=1)=[CH:15][CH:16]=[CH:17][CH:18]=3)([O-:4])=[O:2]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 962WaterHCID 6836N-ethyl carbazole

Product 1

HCID 665739-ethyl-3-nitro-9H-carbazoleYield 71%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Conditions

Temperature
40 °C

Procedure

A solution of 7.3 g of 70% nitric acid (81.1 mmol) in 50 ml acetic acid was added dropwise to a cooled (19°-21° C) acetic acid (200 ml) solution of 15.0 g of N-ethylcarbazole (76.9 mmol). The green reaction solution was then heated on a water bath at 40° C for 2 hours. Upon cooling, addition to 400 ml of water gave a light green precipitate wgich was filtered and air dried. Recrystallization from acetone/methanol gave 13.1 g (71% yield) of 3-nitro-N-ethylcarbazole, mp 118.5°-20° C; the sulfur content (X-ray) was found to be <20 ppm, so that the sulfur in N-ethylcarbazole must be in the elemental or organic (no inorganic) form, most likely the latter, and is easily oxidized to a water soluble form.

Workup

  1. temperatureUpon cooling
  2. customgave a light green precipitate wgich
  3. filtrationwas filtered
  4. customair dried
  5. customRecrystallization from acetone/methanol

Sources & evidence

ORD record
ord-b5d49c6d062e43daaa529c4347e723b0
Source dataset
uspto-grants-1978_09
Patent number
US04111850

Linked notes

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