Ammonia → 2-Propoxyaniline

HRID 67242

Reaction equation

HRID 67242 reaction equation
Cl.C(O)C.[CH2:5]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[N+:15]([O-])=O)[CH2:6][CH3:7].N>[Fe].O>[CH2:5]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[NH2:15])[CH2:6][CH3:7]

Participants

7

Reactant 4

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 702EthanolHCID 5874971-Nitro-2-propoxybenzene

Product 1

HCID 21134322-PropoxyanilineYield 74%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Conditions

Temperature
30 °C

Procedure

Iron 60 mesh (134.5 g., 2.40 mole), concentrated HCl (37.4 cc), ethanol (630 cc), and water (570 cc) are stirred under nitrogen and the temperature of the mixture is raised to reflux. Then o-propoxynitrobenzene (12.5 g., 0.69 mole), is added at reflux over a period of 5 hrs. and refluxed for 3-4 hrs. Then the mixture is neutralized with concentrated ammonia to a pH of 8-9. The temperature is raised to 30° C., and the reaction mass filtered, 200 cc ether added, the organic layer separated. The product distilled at vapor temperature of 65°-67° C. at 0.05-0.03 mm. yielding 77 g of product (74%).

Workup

  1. temperaturethe temperature of the mixture is raised
  2. temperatureto reflux
  3. temperatureat reflux over a period of 5 hrs
  4. temperatureand refluxed for 3-4 hrs
  5. filtrationthe reaction mass filtered
  6. addition200 cc ether added
  7. customthe organic layer separated
  8. distillationThe product distilled at vapor temperature of 65°-67° C. at 0.05-0.03 mm

Sources & evidence

ORD record
ord-705d73ec38b3401f83c100f1fa09f482
Source dataset
uspto-grants-1982_08
Patent number
US04345937

Linked notes

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