Nitric Acid → 7-nitro-9H-indeno[2,1-b]pyridine

HRID 521015Notes

Reaction equation

HRID 521015 reaction equation
[N+:1]([O-:4])(O)=[O:2].[N:5]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:16]=3[CH2:17][C:6]=12>S(=O)(=O)(O)O>[N+:1]([C:14]1[CH:13]=[CH:12][C:11]2[C:7]3[C:6](=[N:5][CH:10]=[CH:9][CH:8]=3)[CH2:17][C:16]=2[CH:15]=1)([O-:4])=[O:2]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 12226515Azafluorene

Product 1

HCID 126342947-nitro-9H-indeno[2,1-b]pyridine

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Procedure

A ca. 10° C.-cold mixture of nitric acid (65%, 1.1 mL) and sulfuric acid (96%, 1.6 mL) is added dropwise to a solution of 9H-indeno[2,1-b]pyridine (2.44 g) in sulfuric acid (96%, 3 mL) chilled in an ice bath. The solution is stirred in the cooling bath for 1 h and poured then onto crushed ice. The precipitate formed is separated by filtration and the filtrate is neutralized using 4 M aqueous NaOH solution. The precipitate formed is separated by filtration and combined with the precipitate separated before. The precipitate is triturated with acetone and dried to give the title compound as a solid. Yield: 2.64 g (85% of theory); LC (method 1): tR=2.93 min; Mass spectrum (ESI+): m/z=213 [M+H]+.

Workup

  1. temperaturechilled in an ice bath
  2. additionpoured
  3. customonto crushed ice
  4. customThe precipitate formed
  5. customis separated by filtration
  6. customThe precipitate formed
  7. customis separated by filtration
  8. customseparated before
  9. customThe precipitate is triturated with acetone
  10. customdried

Sources & evidence

ORD record
ord-9e2683d968774ba39753802a55457529
Source dataset
uspto-grants-2016_05
Patent number
US09328072B2

Reaction notes

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