Iodine → 2-Propenoic acid, 3-(2-aminophenyl)-, ethyl ester, (2E)-

HRID 1605693Notes

Reaction equation

HRID 1605693 reaction equation
[Mg].Br[C:3]1C=C[CH:6]=[CH:5][CH:4]=1.II.CI.[C:13]([CH2:15][C:16](OCC)=O)#[N:14].S(=O)(=O)(O)[OH:22].[CH3:26][CH2:27][O:28][CH2:29][CH3:30]>>[NH2:14][C:13]1[CH:15]=[CH:16][CH:6]=[CH:5][C:4]=1[CH:3]=[CH:26][C:27]([O:28][CH2:29][CH3:30])=[O:22]

Participants

8

Reactant 7

HCID 807IodineHCID 1118Sulfuric AcidHCID 3283Diethyl Ether2×HCID 6328Methyl iodideHCID 7764Ethyl cyanoacetateHCID 7961BromobenzeneHCID 5462224Magnesium2×

Product 1

HCID 27490502-Propenoic acid, 3-(2-aminophenyl)-, ethyl ester, (2E)-

Procedure

To a solution of dry ethyl ether (300 ml.) is added magnesium turnings (16.9 g.). Bromobenzene (103 g.) in ether (600 ml.) is added at a rate to maintain gentle refluxing (An iodine crystal or a ml. of methyliodide often must be added to initiate the reaction.). Refluxing is continued until most of the magnesium has reacted. Ethyl cyanoacetate (30 g.) is added over a 30 minute period and the reaction mixture allowed to stir for 3 hours at room temperature after which time 3.5N sulfuric acid (180 ml.) is added and the reaction allowed to stir for 30 additional minutes. The aqueous layer is extracted with diethyl ether and the organic layer washed with water and dried over sodium sulfate. Removal of the ether in vacuo followed by distillation of the residual oil gives the desired product, b.p. at 0.4 mm, 138°-142° C.

Workup

  1. temperatureto maintain gentle
  2. customthe reaction
  3. temperatureRefluxing
  4. customhas reacted
  5. additionis added
  6. extractionThe aqueous layer is extracted with diethyl ether
  7. washthe organic layer washed with water
  8. dry with materialdried over sodium sulfate
  9. customRemoval of the ether in vacuo
  10. distillationfollowed by distillation of the residual oil

Sources & evidence

ORD record
ord-b91465bdf90443509102eb21b5be17b8
Source dataset
uspto-grants-1976_04
Patent number
US03950525

Reaction notes

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