Ammonium Chloride → HCID 66961501, compound

HRID 2247475Notes

Reaction equation

HRID 2247475 reaction equation
[Cl-].[NH4+].[CH2:3]([O:5][C:6](=[O:20])/[CH:7]=[CH:8]/[C:9]1[CH:10]=[N:11][C:12]([N+:17]([O-])=O)=[C:13]([O:15][CH3:16])[CH:14]=1)[CH3:4]>C(O)C.O.[Fe]>[CH2:3]([O:5][C:6](=[O:20])/[CH:7]=[CH:8]/[C:9]1[CH:10]=[N:11][C:12]([NH2:17])=[C:13]([O:15][CH3:16])[CH:14]=1)[CH3:4]

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 66960160HCID 66960160, compound

Product 1

HCID 66961501HCID 66961501, compoundYield 73%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Iron (1.6 g) and ammonium chloride (3 g) were added to the suspension of (E)-3-(5-methoxy-6-nitropyridin-3-yl)acrylic acid ethyl ester (787 mg) in ethanol (40 mL) and water (8 mL) obtained above, and the reaction solution was heated to reflux for 1 hour. After the reaction solution was allowed to be cooled to room temperature, deposited substance was filtered by celite. Ethyl acetate and saturated sodium bicarbonate water were added to the filtrate, and the organic layer was partitioned. After drying the obtained organic layer with anhydrous magnesium sulfate, the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (elution solvent: heptane-ethyl acetate 2:1), and 506 mg (66%) (E)-3-(6-amino-5-methoxypyridin-3-yl)acrylic acid ethyl ester was obtained. The physical properties of the compound are as follows.

Workup

  1. customobtained above, and the reaction solution
  2. temperaturewas heated
  3. temperatureto reflux for 1 hour
  4. filtrationwas filtered by celite
  5. additionEthyl acetate and saturated sodium bicarbonate water were added to the filtrate
  6. customthe organic layer was partitioned
  7. dry with materialAfter drying the obtained organic layer with anhydrous magnesium sulfate
  8. customthe solvent was evaporated under reduced pressure
  9. customThe obtained residue was purified by silica gel column chromatography (elution solvent: heptane-ethyl acetate 2:1)

Sources & evidence

ORD record
ord-08b25dbb7aa64752b7762217dc675ddf
Source dataset
uspto-grants-2010_03
Patent number
US07687640B2

Reaction notes

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