2-Chloro-3-nitropyridine → N-(2H-1,3-Benzodioxol-5-yl)-3-nitropyridin-2-amine

HRID 333553Notes

Reaction equation

HRID 333553 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[CH2:11]1[O:20][C:19]2[CH:18]=[CH:17][C:15]([NH2:16])=[CH:14][C:13]=2[O:12]1.C([O-])(=O)C.[Na+]>C(O)(=O)C>[O:20]1[C:19]2[CH:18]=[CH:17][C:15]([NH:16][C:2]3[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=3)=[CH:14][C:13]=2[O:12][CH2:11]1

Participants

5

Reactant 3

HCID 796132-Chloro-3-nitropyridineHCID 843101,3-Benzodioxol-5-amineHCID 517045Sodium Acetate

Product 1

HCID 12445382N-(2H-1,3-Benzodioxol-5-yl)-3-nitropyridin-2-amineYield 67%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A 500 mL round bottom flask was charged with 2-chloro-3-nitropyridine (12.0 g, 76.0 mmol), 3,4-(methylenedioxy)aniline (12.97 g, 95.0 mmol), sodium acetate (7.76 g, 95.0 mmol) and acetic acid (200 mL). This was stirred at reflux for 6 h. The solvent was evaporated on a rotovap, and the crude product was column chromatographed with silica gel using a mobile phase gradient of 50-100% dichloromethane in hexane to give N-(benzo[d][1,3]dioxol-5-yl)-3-nitropyridin-2-amine (13.1 g, 67%) as a red solid.

Workup

  1. temperatureat reflux for 6 h
  2. customThe solvent was evaporated on a rotovap
  3. customchromatographed with silica gel using a mobile phase gradient of 50-100% dichloromethane in hexane

Sources & evidence

ORD record
ord-548d5730f19743bdae8a21964653c9bd
Source dataset
uspto-grants-2014_11
Patent number
US08883322B2

Reaction notes

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