Ammonia → 2-Propoxyaniline

HRID 1447739

Reaction equation

HRID 1447739 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-cc2c2f40825047728d7dbfdaff95c77c
Source dataset
uspto-grants-1979_12
Patent number
US04178167

Linked notes

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