Hydrochloric Acid → HCID 54459639, compound

HRID 1395113Notes

Reaction equation

HRID 1395113 reaction equation
O.Cl.[CH:3]([O:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[N+:13]([O-])=O)=[CH:4][CH3:5].[OH-].[NH4+]>[Fe].C(O)C>[CH:3]([O:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[NH2:13])=[CH:4][CH3:5]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14923Ammonium HydroxideHCID 54051739HCID 54051739, compound

Product 1

HCID 54459639HCID 54459639, compoundYield 67.2%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Procedure

Iron 60 mesh (106.3 g, 1.9 mole), water (450 cc), ethanol (500 cc) and concentrated hydrochloric acid (29.5 cc) were heated to reflux under a nitrogen blanket. Then 2-prop-1-en-oxynitrobenzene (89.6 g, 0.57 mole) was added at reflux over a period of 2 hours. The reaction was maintained at reflux over a period of 2 hours. The reaction was maintained at reflux for an additional 3 hours. 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 110°-112° C. at 4.5 mm. Hg to yield 50.1 g (67.2%) of product.

Workup

  1. temperatureto reflux under a nitrogen blanket
  2. temperatureat reflux over a period of 2 hours
  3. temperatureThe reaction was maintained
  4. temperatureat reflux over a period of 2 hours
  5. temperatureThe reaction was maintained
  6. temperatureat reflux for an additional 3 hours
  7. filtrationThe reaction mixture then was filtered at 30° C.
  8. washthe filtrate was washed with 200 cc of ether
  9. extractionThe filtrate was extracted with 4×50 cc of ether
  10. customthe combined ether extracts were subjected to rotary evaporation
  11. distillationThe crude product was fractionally distilled at 110°-112° C. at 4.5 mm. Hg

Sources & evidence

ORD record
ord-161c24e67fc948e2a135f79776013446
Source dataset
uspto-grants-1980_05
Patent number
US04202821

Reaction notes

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