Ethanol → Ethyl 2-(2-amino-3-phenoxyphenyl)acetate

HRID 2418343Notes

Reaction equation

HRID 2418343 reaction equation
[Cl-].[NH4+].C(O)C.[N+:6]([C:9]1[C:14]([O:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:13][CH:12]=[CH:11][C:10]=1[CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])([O-])=O>[Fe].O>[NH2:6][C:9]1[C:14]([O:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:13][CH:12]=[CH:11][C:10]=1[CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24]

Participants

6

Reactant 3

HCID 702EthanolHCID 25517Ammonium ChlorideHCID 20446288Ethyl 2-(2-nitro-3-phenoxyphenyl)acetate

Product 1

HCID 20446209Ethyl 2-(2-amino-3-phenoxyphenyl)acetate

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Procedure

To a mixture of iron powder (9 g.), ammonium chloride (0.9 g.), ethanol (80 ml.) and water (40 ml.) was added ethyl 2-(2-nitro-3-phenoxyphenyl)acetate (10.9 g.) over 5 minutes under mild reflux and stirring and the mixture was stirred for 1.5 hours at the same temperature. The reaction mixture was filtered under heating and ethanol was distilled off from the filtrate under reduced pressure. To the residue was added water and the mixture was extracted with diethyl ether. The extract was washed with water and dried over magnesium sulfate, and diethyl ether was distilled off under reduced pressure to give the viscous captioned compound (9.5 g.).

Workup

  1. temperatureunder mild reflux
  2. stirringthe mixture was stirred for 1.5 hours at the same temperature
  3. filtrationThe reaction mixture was filtered
  4. temperatureunder heating
  5. distillationethanol was distilled off from the filtrate under reduced pressure
  6. additionTo the residue was added water
  7. extractionthe mixture was extracted with diethyl ether
  8. washThe extract was washed with water
  9. dry with materialdried over magnesium sulfate, and diethyl ether
  10. distillationwas distilled off under reduced pressure
  11. customto give the viscous captioned compound (9.5 g.)

Sources & evidence

ORD record
ord-7d9dc1140c1e4630943b8fa453c2b800
Source dataset
uspto-grants-1984_09
Patent number
US04472433

Reaction notes

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