Hydrochloric Acid → HCID 53828559, compound

HRID 461766Notes

Reaction equation

HRID 461766 reaction equation
[Cl:1][C:2](Cl)([C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([N+:13]([O-])=O)[CH:8]=1)[C:3](Cl)([Cl:5])[CH3:4].Cl>[Fe].C(O)C>[Cl:1][C:2]([C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([NH2:13])[CH:8]=1)=[C:3]([Cl:5])[CH3:4]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 21392405HCID 21392405, compound

Product 1

HCID 53828559HCID 53828559, compound

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent2×

Procedure

13 G. of 1,1,2,2-tetrachloro-1-(3-nitrophenyl) propane and 7.9 g. of iron powder is stirred vigorously under reflux in 465 ml. of 50% aqueous ethanol. 5.6 Ml of a solution prepared prejviously from 52 ml. of concentrated hydrochloric acid and 250 ml. of 50% aqueous ethanol are added dropwise over 5 minutes. After an additional 2 hours of stirring at reflux temperature, the hot reaction mixture is filtered, cooled to room temperature, diluted with enough chloroform to double the volume of the ethanol, and made basic with saturated aqueous sodium bicarbonate solution. The organic layer is separated, washed with water, dried and concentrated in vacuo to give a mixture of essentially pure cis and trans 1,2-dichloro-1-(3-aminophenyl)-1-propene as a yellow oil.

Workup

  1. temperatureunder reflux in 465 ml
  2. custom5.6 Ml of a solution prepared prejviously from 52 ml
  3. temperatureat reflux temperature
  4. filtrationthe hot reaction mixture is filtered
  5. additiondiluted with enough chloroform
  6. customThe organic layer is separated
  7. washwashed with water
  8. customdried
  9. concentrationconcentrated in vacuo
  10. customto give

Sources & evidence

ORD record
ord-b2baa7db13b142e99bc14412ac50b5f1
Source dataset
uspto-grants-1977_12
Patent number
US04064239

Reaction notes

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