Nitric Acid → 2,6-Dichloro-3-nitropyridin-4-amine

HRID 343779

Reaction equation

HRID 343779 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[C:4]([Cl:9])[CH:3]=1.[N+:10]([O-])([OH:12])=[O:11].[OH-].[Na+]>OS(O)(=O)=O>[NH2:1][C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[C:4]([Cl:9])[C:3]=1[N+:10]([O-:12])=[O:11]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 14798Sodium HydroxideHCID 1376524-Amino-2,6-dichloropyridine

Product 1

HCID 2827402,6-Dichloro-3-nitropyridin-4-amineYield 77.1%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
55 °C

Procedure

To a solution of 4-amino-2,6-dichloropyridine (1.07 g, 6.56 mmol) in conc H2SO4 (3.5 mL) was added 0.50 mL of 70% HNO3 (7.94 mmol) at room temperature. The mixture was stirred at 55° C. for 15 h, then poured into ice-H2O (70 mL). To this mixture was added 40% aq. NaOH slowly to adjust the pH to 10. The precipitate was filtered, washed with water and dried to give 1.052 g (77%) of 23 as a pale yellow powder, mp 136°-8° C. 1H NMR (CDCl3) δ 6.116 (bs, 2H), 6.750 (s, 1H). It was used for the next reaction without further purification.

Workup

  1. filtrationThe precipitate was filtered
  2. washwashed with water
  3. customdried

Sources & evidence

ORD record
ord-f42a47440d0d4083baed06e27cdd7727
Source dataset
uspto-grants-1999_01
Patent number
US05863916

Linked notes

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