Water → 2-(4-Chlorophenylmethylamino)-3-nitro-5-chloropyridine

HRID 653664Notes

Reaction equation

HRID 653664 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][NH2:7])=[CH:4][CH:3]=1.Cl[C:11]1[C:16]([N+:17]([O-:19])=[O:18])=[CH:15][C:14]([Cl:20])=[CH:13][N:12]=1.O>C1(C)C(C)=CC=CC=1.CC1C=CC(CC)=CN=1>[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][NH:7][C:11]2[C:16]([N+:17]([O-:19])=[O:18])=[CH:15][C:14]([Cl:20])=[CH:13][N:12]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 962WaterHCID 660364-ChlorobenzylamineHCID 80633312,5-Dichloro-3-nitropyridine

Product 1

HCID 110664382-(4-Chlorophenylmethylamino)-3-nitro-5-chloropyridineYield 87%

Reagents, catalysts & solvents 2

HCID 7237O-XyleneSolventHCID 77285-Ethyl-2-methylpyridineSolvent

Procedure

A solution of 20.9 g of 4-chlorobenzylamine and 15.7 g of 2,5-dichloro-3-nitropyridine in 250 ml of xylene and 20 ml of 2-methyl-5-ethylpyridine is refluxed for 30 hours. After cooling, water is added to the reaction mixture, the resulting mixture is then extracted with ethyl acetate and the organic phase is washed with a dilute solution of hydrochloric acid and dried over magnesium sulfate. The solvent is evaporated off under vacuum and the residue obtained crystallizes from isopropyl ether to give 21.1 g of 2-(4-chlorophenylmethylamino)-3-nitro-5-chloropyridine in the form of crystals melting at 120° C.

Workup

  1. temperatureAfter cooling
  2. extractionthe resulting mixture is then extracted with ethyl acetate
  3. washthe organic phase is washed with a dilute solution of hydrochloric acid
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent is evaporated off under vacuum
  6. customthe residue obtained
  7. customcrystallizes from isopropyl ether

Sources & evidence

ORD record
ord-84a6714208144e968df5e532ad3dcb22
Source dataset
uspto-grants-1992_07
Patent number
US05128359

Reaction notes

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