Nitric Acid → 3-Chloro-6-(2-nitrophenyl)pyridazine

HRID 747923Notes

Reaction equation

HRID 747923 reaction equation
[Cl:1][C:2]1[N:3]=[N:4][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:6][CH:7]=1.[N+:14]([O-])([OH:16])=[O:15].[OH-].[Na+]>S(=O)(=O)(O)O>[Cl:1][C:2]1[N:3]=[N:4][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[N+:14]([O-:16])=[O:15])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 14798Sodium HydroxideHCID 885153-Chloro-6-phenylpyridazine

Product 1

HCID 133622073-Chloro-6-(2-nitrophenyl)pyridazine

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

To an ice-cold solution of 3-chloro-6-phenylpyridazine (Aldrich, 1.4 g, 7.5 mmol) in conc. sulfuric acid (30 mL) was added 90% nitric acid (0.6 mL, 15 mmol). After 15 min. the mixture was poured over ice (200 mL) and neutralized with 25% aq. NaOH. The resulting precipitate was collected by filtration and dried under vacuum. The crude product (1.84 g) was a 1:1:0.5 mixture of ortho:meta para isomers.

Workup

  1. filtrationThe resulting precipitate was collected by filtration
  2. customdried under vacuum
  3. additiona 1:1:0.5 mixture of ortho

Sources & evidence

ORD record
ord-aa21c4dfdd984ec894f82f2169b530a5
Source dataset
uspto-grants-2008_07
Patent number
US07399765B2

Reaction notes

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