Ammonium Chloride → HCID 59444053, compound

HRID 1969006Notes

Reaction equation

HRID 1969006 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5](/[CH:8]=[CH:9]/[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[C:4]([N+:15]([O-])=O)[CH:3]=1.[Cl-].[NH4+]>C(O)C.O.[Fe]>[NH2:15][C:4]1[CH:3]=[C:2]([CH3:1])[CH:7]=[CH:6][C:5]=1/[CH:8]=[CH:9]/[C:10]([O:12][CH2:13][CH3:14])=[O:11]

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 24801705HCID 24801705, compound

Product 1

HCID 59444053HCID 59444053, compoundYield 96%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Ethyl (2E)-3-(4-methyl-2-nitrophenyl)-2-propenoate D141 (0.500 g, 2.126 mmol), iron (0.593 g, 10.63 mmol) and ammonium chloride (0.057 g, 1.063 mmol) in ethanol (11 mL) and water (2 mL) was heated at reflux for 2 hours. The mixture was cooled and filtered through a pad of kieselguhr. The filtrate was concentrated and the residue diluted with ethyl acetate, washed with water and dried (MgSO4). Filtration and evaporation of solvent afforded a bright yellow solid (0.417 g, 96%).

Workup

  1. temperatureat reflux for 2 hours
  2. temperatureThe mixture was cooled
  3. filtrationfiltered through a pad of kieselguhr
  4. concentrationThe filtrate was concentrated
  5. additionthe residue diluted with ethyl acetate
  6. washwashed with water
  7. dry with materialdried (MgSO4)
  8. filtrationFiltration and evaporation of solvent

Sources & evidence

ORD record
ord-eb3e228c5b874b56b211b219427f11d1
Source dataset
uspto-grants-2013_04
Patent number
US08426443B2

Reaction notes

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