Water → (2-Chloro-5-nitro-pyridin-4-yl)-(4-methoxyphenyl)-amine

HRID 1394227Notes

Reaction equation

HRID 1394227 reaction equation
[C:1]1([O:7][CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl:9][C:10]1[CH:15]=[C:14](Cl)[C:13]([N+:17]([O-:19])=[O:18])=[CH:12][N:11]=1.C([N:22](CC)CC)C.O>C1COCC1>[Cl:9][C:10]1[CH:15]=[C:14]([NH:22][C:4]2[CH:5]=[CH:6][C:1]([O:7][CH3:8])=[CH:2][CH:3]=2)[C:13]([N+:17]([O-:19])=[O:18])=[CH:12][N:11]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7519AnisoleHCID 8471TriethylamineHCID 122757652,4-Dichloro-5-nitropyridine

Product 1

HCID 85868869(2-Chloro-5-nitro-pyridin-4-yl)-(4-methoxyphenyl)-amine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Anisole (908 mg, 7.4 mmol) was added to a solution of 2,4-dichloro-5-nitropyridine (1.30 g, 6.7 mmol) and triethylamine (1.02 mL, 7.4 mmol) in THF (5 mL). The mixture was allowed to stir at rt for 1 h, then was poured into H2O and extracted with EtOAc. The organic layers were washed with H2O and brine, dried, filtered and concentrated to a residue which was purified by column chromatography (5-50% EtOAc in hex) to give the title compound as an orange solid, 1.46 g (78%). MS (ES+) m/e 280 [M+H]+.

Workup

  1. extractionextracted with EtOAc
  2. washThe organic layers were washed with H2O and brine
  3. customdried
  4. filtrationfiltered
  5. concentrationconcentrated to a residue which
  6. customwas purified by column chromatography (5-50% EtOAc in hex)

Sources & evidence

ORD record
ord-41bc4d349db54c4a81b89cc468e6bf86
Source dataset
uspto-grants-2008_03
Patent number
US07348339B2

Reaction notes

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