Hydrochloric Acid → 2-(Cyclopentyloxy)aniline

HRID 262013

Reaction equation

HRID 262013 reaction equation
O.Cl.[CH:3]1([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[N+:15]([O-])=O)[CH2:7][CH2:6][CH2:5][CH2:4]1.[OH-].[NH4+]>[Fe].C(O)C>[CH:3]1([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[NH2:15])[CH2:7][CH2:6][CH2:5][CH2:4]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14923Ammonium HydroxideHCID 221644731-(Cyclopentyloxy)-2-nitrobenzene

Product 1

HCID 64853982-(Cyclopentyloxy)anilineYield 64.3%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Procedure

Iron 60 mesh (51.9 g, 0.93 mole), water (220 cc), ethanol (244 cc) and concentrated hydrochloric acid (14.2 cc) were heated to reflux under a nitrogen blanket. Then 2-cyclopentoxynitrobenzene (55.2 g, 0.27 mole) was added at reflux over a period of 2 hrs. The reaction was maintained at reflux for an additional 3 hrs. The pH was adjusted to 7-8 by the addition of concentrated ammonium hydroxide. The reaction mixture then was filtered at 30° C., and the filtrate was washed with 200 cc of ether. The filtrate was extracted with 4×50 cc of ether and the combined ether extracts were subjected to rotary evaporation. The crude product was fractionally distilled at 126°-130° C. at 2.0-2.5 mm. Hg to yield 30.3 g (64.3%) of product.

Workup

  1. temperatureto reflux under a nitrogen blanket
  2. temperatureat reflux over a period of 2 hrs
  3. temperatureThe reaction was maintained
  4. temperatureat reflux for an additional 3 hrs
  5. filtrationThe reaction mixture then was filtered at 30° C.
  6. washthe filtrate was washed with 200 cc of ether
  7. extractionThe filtrate was extracted with 4×50 cc of ether
  8. customthe combined ether extracts were subjected to rotary evaporation
  9. distillationThe crude product was fractionally distilled at 126°-130° C. at 2.0-2.5 mm. Hg

Sources & evidence

ORD record
ord-1e7a2f2e3f274eda8f2e6befe225e3e4
Source dataset
uspto-grants-1979_05
Patent number
US04153446

Linked notes

Loading…