Ammonium Chloride → HCID 9928714, compound

HRID 1274364Notes

Reaction equation

HRID 1274364 reaction equation
[CH2:1]([O:8][C:9]1[CH:26]=[CH:25][C:12]([O:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][C:15]=2[N+:22]([O-])=O)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl-:27].[NH4+]>C(O)C.O.[Fe]>[ClH:27].[CH2:1]([O:8][C:9]1[CH:26]=[CH:25][C:12]([O:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][C:15]=2[NH2:22])=[CH:11][CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 22120987HCID 22120987, compound

Product 1

HCID 9928714HCID 9928714, compoundYield 86.5%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of 4-[4-(benzyloxy)phenoxy]-3-nitroanisole (1.23 g, 3.5 mmol) in ethanol (20 ml) were added an iron powder (0.90 g, 16.1 mg-atom) and a solution of ammonium chloride (0.11 g, 2.1 mmol) in water (2 ml), followed by reflux for 3 hours. The insoluble matter was filtered, and the filtrate was poured into water, followed by extraction with ethyl acetate. The organic layer was washed with water, then with a saturated aqueous sodium chloride solution and dried, and thereafter the solvent was evaporated under reduced pressure. The residue was dissolved in a small amount of ethyl acetate, and the resulting solution was, after addition of 4N-hydrogen chloride/acetic acid solution (2 ml), stirred for 30 minutes. The precipitating crystals were collected by filtration and dried under reduced pressure to give the title compound (0.65 g).

Workup

  1. temperatureby reflux for 3 hours
  2. filtrationThe insoluble matter was filtered
  3. additionthe filtrate was poured into water
  4. extractionfollowed by extraction with ethyl acetate
  5. washThe organic layer was washed with water
  6. dry with materialwith a saturated aqueous sodium chloride solution and dried
  7. customthe solvent was evaporated under reduced pressure
  8. dissolutionThe residue was dissolved in a small amount of ethyl acetate
  9. additionafter addition of 4N-hydrogen chloride/acetic acid solution (2 ml)
  10. filtrationThe precipitating crystals were collected by filtration
  11. customdried under reduced pressure

Sources & evidence

ORD record
ord-04bc17cc5ec7491aafe7f91b0e094c67
Source dataset
uspto-grants-2000_12
Patent number
US06156801

Reaction notes

Loading…