Hydrochloric Acid → HCID 86684676, compound

HRID 75539Notes

Reaction equation

HRID 75539 reaction equation
[CH3:1][O:2][C:3]1[C:8]([C:9]([O:16]CC)=[CH:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:7][CH:6]=[C:5]([O:19][CH3:20])[N:4]=1.Cl.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[CH3:1][O:2][C:3]1[C:8]([C:9](=[O:16])[CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:7][CH:6]=[C:5]([O:19][CH3:20])[N:4]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 86684677Ethyl 3-(2,6-dimethoxypyridin-3-yl)-3-ethoxyacrylate

Product 1

HCID 86684676HCID 86684676, compoundYield 95.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of ethyl 3-(2,6-dimethoxypyridin-3-yl)-3-ethoxyacrylate (600 mg, 2.13 mmol) in CH2Cl2 (18 mL) was gradually added 3N aqueous HCl (3.5 mL). The reaction mixture was stirred at room temperature for 2 hours, then carefully added to a saturated sodium bicarbonate solution (30 mL). The layers were separated and the aqueous layer was extracted with CH2Cl2. The combined organic extracts were passed though a plug of cotton to dry and concentrated in vacuo. The resulting oil was purified by flash chromatography (0-60% EtOAc/heptanes) to provide the title compound (515 mg, 95% yield) as a white solid.

Workup

  1. customThe layers were separated
  2. extractionthe aqueous layer was extracted with CH2Cl2
  3. customto dry
  4. concentrationconcentrated in vacuo
  5. customThe resulting oil was purified by flash chromatography (0-60% EtOAc/heptanes)

Sources & evidence

ORD record
ord-29bfeac4ed5640ca94add37d2e23703d
Source dataset
uspto-grants-2014_09
Patent number
US08835449B2

Reaction notes

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