Hydrochloric Acid → HCID 23593812, compound

HRID 1611969Notes

Reaction equation

HRID 1611969 reaction equation
[CH2:1]([O:3][C:4]1[C:5]([N+:10]([O-:12])=[O:11])=[N:6][CH:7]=[CH:8][CH:9]=1)[CH3:2].Cl[CH:14]([CH3:20])[C:15]([O:17][CH2:18][CH3:19])=[O:16].[H-].[Na+].[CH3:23]OS(OC)(=O)=O.Cl>CN(C=O)C.CCOC(C)=O>[CH2:18]([O:17][C:15](=[O:16])[C:14]([C:8]1[CH:7]=[N:6][C:5]([N+:10]([O-:12])=[O:11])=[C:4]([O:3][CH2:1][CH3:2])[CH:9]=1)([CH3:20])[CH3:23])[CH3:19]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 6497Dimethyl SulfateHCID 10807Ethyl 2-chloropropionateHCID 24758Sodium hydrideHCID 52866Pyridine, 3-ethoxy-2-nitro-

Product 1

HCID 23593812HCID 23593812, compoundYield 66.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 3-ethoxy-2-nitro-pyridine (0.84 g) and ethyl 2-chloropropionate (2.1 g) in DMF (8 mL) was added dropwise to a slurry of sodium hydride (0.6 g, 60% suspension in oil) in DMF (8 mL) while cooling at 0–5° C. The resulting purple-colored solution was stirred at 0–5° C. for one hr., and then at room temperature for two hrs. Dimethylsulfate (0.89 g) was added to the solution and the reaction mixture was shaken overnight. The resulting amber-colored solution was poured onto a mixture of 1N aqueous hydrogen chloride (20 mL), ice water (20 mL), and EtOAc (50 mL), and the phases were separated. The organic phase was washed with 1N aqueous sodium hydroxide, water, and brine. The solvent was evaporated to give an amber-colored oil (933 mg), which was purified by flash chromatography on silica gel, eluting with 1:4 ethyl acetate/hexanes to give 389 mg (28% yield) of a pale yellow oil. AP/MS+=283.

Workup

  1. temperaturewhile cooling at 0–5° C
  2. wait, and then at room temperature for two hrs
  3. stirringthe reaction mixture was shaken overnight
  4. customthe phases were separated
  5. washThe organic phase was washed with 1N aqueous sodium hydroxide, water, and brine
  6. customThe solvent was evaporated

Sources & evidence

ORD record
ord-0a947a7908864db99ff0162fe7ffe6ac
Source dataset
uspto-grants-2006_01
Patent number
US06992092B2

Reaction notes

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