Water → 5-Chloro-3-(2-methoxy-ethoxy)-2-nitro-pyridine

HRID 1966215Notes

Reaction equation

HRID 1966215 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([OH:11])[C:5]([N+:8]([O-:10])=[O:9])=[N:6][CH:7]=1.[H-].[Na+].Br[CH2:15][CH2:16][O:17][CH3:18].O>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([O:11][CH2:15][CH2:16][O:17][CH3:18])[C:5]([N+:8]([O-:10])=[O:9])=[N:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 809722-Bromoethyl methyl etherHCID 187656985-Chloro-2-nitropyridin-3-ol

Product 1

HCID 674861005-Chloro-3-(2-methoxy-ethoxy)-2-nitro-pyridineYield 60%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5-Chloro-2-nitro-pyridine-3-ol (1.15 mmol) is dissolved in DMF (2 ml) and NaH (1.4 eq., 60% suspension in liquid paraffin) is added and the suspension is stirred 45 min at room temperature. 1-Bromo-2-methoxy-ethane (1 eq.) is added and the reaction suspension is heated to 100° C. for 24 hours. The reaction solution is pored into water and extracted with dichloromethane. The combined organic layers are washed with brine, dried over MgSO4 and the solvent is removed in vacuo. 5-Chloro-3-(2-methoxy-1-ethoxy)-2-nitro-pyridine is obtained after column chromatography as beige solid in a yield of 60%; mp. 71.5-72.5°; HPLC (method C): 1.63 min; LC-MS (method A): 1.36 min, 232.95 (M+H+).

Workup

  1. temperaturethe reaction suspension is heated to 100° C. for 24 hours
  2. extractionextracted with dichloromethane
  3. washThe combined organic layers are washed with brine
  4. dry with materialdried over MgSO4
  5. customthe solvent is removed in vacuo

Sources & evidence

ORD record
ord-0511458e3448496a926549efafb5bbb9
Source dataset
uspto-grants-2013_04
Patent number
US08420642B2

Reaction notes

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