Ammonium Chloride → HCID 20708738, compound

HRID 494966Notes

Reaction equation

HRID 494966 reaction equation
[CH2:1]([C:4]1[CH:9]=[C:8]([N+:10]([O-])=O)[CH:7]=[CH:6][C:5]=1[O:13][CH3:14])[CH:2]=[CH2:3].[Cl-].[NH4+]>C(O)C.O.[Fe]>[CH2:1]([C:4]1[CH:9]=[C:8]([CH:7]=[CH:6][C:5]=1[O:13][CH3:14])[NH2:10])[CH:2]=[CH2:3]

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 57682798HCID 57682798, compound

Product 1

HCID 20708738HCID 20708738, compoundYield 87.6%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

15.0 g of 1-allyl-2-methoxy-5-nitrobenzene, 33.4 g of ammonium chloride, and 17.5 g of iron were suspended in 270 ml of ethanol and 55 ml of water. The reaction solution was heated to reflux for 1 hour. Thereafter, the reaction solution was cooled to a room temperature, and insoluble matters were then removed by filtration. The filtrate was concentrated under a reduced pressure. The residue was diluted with ethyl acetate and then washed with a saturated sodium bicarbonate aqueous solution and a saturated sodium chloride aqueous solution. The organic layer was dried over magnesium sulfate and then concentrated under a reduced pressure. The residue was purified by silica gel column chromatography (hexane-ethyl acetate), so as to obtain 11.1 g of the subject compound.

Workup

  1. temperatureThe reaction solution was heated
  2. temperatureto reflux for 1 hour
  3. custominsoluble matters were then removed by filtration
  4. concentrationThe filtrate was concentrated under a reduced pressure
  5. additionThe residue was diluted with ethyl acetate
  6. washwashed with a saturated sodium bicarbonate aqueous solution
  7. dry with materialThe organic layer was dried over magnesium sulfate
  8. concentrationconcentrated under a reduced pressure
  9. customThe residue was purified by silica gel column chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-d35aec0e3b344b61ba8d758d1b47f48b
Source dataset
uspto-grants-2009_05
Patent number
US07538123B2

Reaction notes

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