Hydrochloric Acid → N-Benzyl-5-nitropyridin-2(1H)-imine

HRID 479848Notes

Reaction equation

HRID 479848 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1.[CH2:11]([NH2:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.Cl>C(O)C>[CH2:11]([NH:18][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 7504BenzylamineHCID 783082-Chloro-5-nitropyridine

Product 1

HCID 261542N-Benzyl-5-nitropyridin-2(1H)-imineYield 88.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2-chloro-5-nitropyridine (1.59 g, 10 mmol) and benzylamine (2.3 mL, 21 mmol) in ethanol (10 mL) was heated at reflux for 2 h. The reaction mixture was allowed to ambient temperature, 1.2 N HCl was added, the precipitate collected, rinsed with water, and dried to give 2.02 g of 2-benzylamino-5-nitropyridine as a yellow solid.

Workup

  1. temperatureat reflux for 2 h
  2. customwas allowed to ambient temperature
  3. customthe precipitate collected
  4. washrinsed with water
  5. customdried

Sources & evidence

ORD record
ord-e3b89971557d4186856e732d6ddf069d
Source dataset
uspto-grants-2003_11
Patent number
US06646124B2

Reaction notes

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