2-Chloro-3-nitropyridine → [2-Chloro-4-(3-nitropyridin-2-ylamino)-phenyl]-acetic acid ethyl ester

HRID 1660958Notes

Reaction equation

HRID 1660958 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]([O:13][C:14](=[O:24])[CH2:15][C:16]1[CH:21]=[CH:20][C:19]([NH2:22])=[CH:18][C:17]=1[Cl:23])[CH3:12]>CCO.O1CCOCC1>[CH2:11]([O:13][C:14](=[O:24])[CH2:15][C:16]1[CH:21]=[CH:20][C:19]([NH:22][C:2]2[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=2)=[CH:18][C:17]=1[Cl:23])[CH3:12]

Participants

4

Reactant 2

HCID 796132-Chloro-3-nitropyridineHCID 59419389Ethyl 2-(4-amino-2-chlorophenyl)acetate

Product 1

HCID 67023632[2-Chloro-4-(3-nitropyridin-2-ylamino)-phenyl]-acetic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 22560076Dioxan ethanolSolvent

Procedure

A mixture of 2-chloro-3-nitro-pyridine (0.600 g, 3.80 mmol) (Aldrich) and (4-amino-2-chloro-phenyl)-acetic acid ethyl ester (see WO 97/21665) (0.800 g 3.80 mmol) in EtOH/dioxane (20 mL; 1:1, v/v) is stirred and refluxed for 72 h. The mixture is allowed to cool to rt and concentrated in vacuo. The crude material is purified by silica gel column chromatography (Hexane/EtOAc, 7/3) to afford a red solid, which upon trituration with Et2O provides the title compound as an orange solid: ES-MS: 336.0 [M+H]+; single peak at tR=5.59 min (System 1); Rf=0.39 (Hexane/EtOAc, 7:3).

Workup

  1. temperaturerefluxed for 72 h
  2. concentrationconcentrated in vacuo
  3. customThe crude material is purified by silica gel column chromatography (Hexane/EtOAc, 7/3)
  4. customto afford a red solid, which upon trituration with Et2O

Sources & evidence

ORD record
ord-708821e500fa445e9232143683d8e788
Source dataset
uspto-grants-2011_10
Patent number
US08030311B2

Reaction notes

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