Acetic Acid → HCID 68528800, compound

HRID 884106Notes

Reaction equation

HRID 884106 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([O:10][C:11]2[CH:16]=[CH:15][C:14]([CH:17]=[CH:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:13][CH:12]=2)=[N:8][CH:9]=1)([O-])=O.[Cl-].[NH4+].C(O)(=O)C>CO.[Zn]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([O:10][C:11]2[CH:16]=[CH:15][C:14]([CH:17]=[CH:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:13][CH:12]=2)=[N:8][CH:9]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 25517Ammonium ChlorideHCID 68524373HCID 68524373, compound

Product 1

HCID 68528800HCID 68528800, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 887MethanolSolvent

Procedure

To a solution of ethyl 3-[4-(5-nitropyridin-2-yloxy)phenyl]acrylate (2.02 g, 6.43 mmol) in methanol (100 mL) were added zinc (6.3 g, 96.3 mmol) and ammonium chloride (710 mg, 13.27 mmol). The resulting reaction solution was stirred for 2.5 hours under reflux, then acetic acid (5 mL) was added, and stirred for 20 minutes under reflux. Insoluble matter was filtered off through Celite, after which the filtrate was concentrated under reduced pressure. To the residue was added 5% potassium hydrogensulfate (150 mL), the mixture was extracted with dichloromethane, and the dichloromethane layer was washed with a saturated sodium bicarbonate solution and brine. The dichloromethane layer was dried over anhydrous magnesium sulfate, and evaporated, to thereby yield 1.78 g of the title compound.

Workup

  1. customThe resulting reaction solution
  2. temperatureunder reflux
  3. stirringstirred for 20 minutes
  4. temperatureunder reflux
  5. filtrationInsoluble matter was filtered off through Celite
  6. concentrationafter which the filtrate was concentrated under reduced pressure
  7. additionTo the residue was added 5% potassium hydrogensulfate (150 mL)
  8. extractionthe mixture was extracted with dichloromethane
  9. washthe dichloromethane layer was washed with a saturated sodium bicarbonate solution and brine
  10. dry with materialThe dichloromethane layer was dried over anhydrous magnesium sulfate
  11. customevaporated

Sources & evidence

ORD record
ord-5f221cd5b2c242188db6889095c30f32
Source dataset
uspto-grants-2012_08
Patent number
US08236826B2

Reaction notes

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