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

HRID 1010726Notes

Reaction equation

HRID 1010726 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 0.600 g of 2-chloro-3-nitro-pyridine (Aldrich) and 0.800 g of (4-amino-2-chloro-phenyl)-acetic acid ethyl ester (see WO 97/21665) in 20 ml of EtOH/dioxane (1:1, v/v) is stirred and refluxed for 72 hours. The mixture obtained is allowed to cool to rt and is concentrated in vacuo. The concentrate obtained is subjected to silica gel column chromatography. A solid is obtained which is triturated with Et2O. [2-Chloro-4-(3-nitro-pyridin-2-ylamino)-phenyl]-acetic acid ethyl ester is obtained in the form of a 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 hours
  2. customThe mixture obtained
  3. concentrationis concentrated in vacuo
  4. customThe concentrate obtained
  5. customA solid is obtained which
  6. customis triturated with Et2O

Sources & evidence

ORD record
ord-5c47b6003100419aba6d8a7f86a18601
Source dataset
uspto-grants-2011_07
Patent number
US07977338B2

Reaction notes

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