Hydrochloric Acid → HCID 86684676, compound

HRID 1056512Notes

Reaction equation

HRID 1056512 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-e069b70350c040b78ec613718977510c
Source dataset
uspto-grants-2016_07
Patent number
US09399626B2

Reaction notes

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