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

HRID 614331Notes

Reaction equation

HRID 614331 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>[CH2:11]1[O:20][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]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-amine

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 6.3 g. (0.04 mole) of 2-chloro-3-nitropyridine, 6.8 g. (0.05 mole) 3,4-methylenedioxyaniline and 4.1 g. (0.05 mole) of sodium acetate in 125 ml. of acetic acid was stirred and refluxed for 5 hours. The reaction mixture was concentrated to about 1/4 of the original volume and diluted with 100 ml. of water. The precipitate was collected (11.5 g.) and a sample was recrystallized from ethanol to give 2-(3,4-methylenedioxyanilino)-3-nitropyridine, m.p. 146°-148° C.

Workup

  1. additionA mixture of 6.3 g
  2. temperaturerefluxed for 5 hours
  3. concentrationThe reaction mixture was concentrated to about 1/4 of the original volume
  4. additiondiluted with 100 ml
  5. customThe precipitate was collected (11.5 g.)
  6. customa sample was recrystallized from ethanol

Sources & evidence

ORD record
ord-9471d208238941a7815c8913503d6596
Source dataset
uspto-grants-1979_03
Patent number
US04144341

Reaction notes

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