Hydrochloric Acid → Ethyl 3-amino-3-phenylprop-2-enoate

HRID 1719610Notes

Reaction equation

HRID 1719610 reaction equation
Cl.COCCOCCOC.II.[CH2:13]([O:15][C:16](=[O:19])[CH2:17]Br)[CH3:14].[C:20](#[N:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>[Zn]>[CH2:13]([O:15][C:16](=[O:19])[CH:17]=[C:20]([NH2:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH3:14]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 807IodineHCID 7505BenzonitrileHCID 7748Ethyl bromoacetateHCID 8150Diglyme

Product 1

HCID 312934Ethyl 3-amino-3-phenylprop-2-enoateYield 95%

Reagents, catalysts & solvents 1

HCID 23994ZincCatalyst2×

Procedure

21 g of (97.2%) zinc dust are treated, according to Example 4, with 2% (by weight) aqueous hydrochloric acid. The zinc activated in this manner is placed into 75 ml of diethylene glycol dimethyl ether, and 0.6 g of iodine is added. There is then added at 25° C. (if necessary with external cooling) a mixture of 16.7 ml of bromoacetic acid ethyl ester and 15.4 ml of benzonitrile. The mixture is stirred for 17 hours at room temperature, and subsequently processed basically analogously to Example 2. The β-aminocinnamic acid ethyl ester is obtained in 95% yield. When in the above Example the solvent diethylene glycol dimethyl ether is replaced by toluene or diethyl ether, the procedure being otherwise the same, there are likewise obtained good yields of β-aminocinnamic acid ethyl ester.

Workup

  1. additionis added
  2. additionThere is then added at 25° C.
  3. temperature(if necessary with external cooling)

Sources & evidence

ORD record
ord-92ca3cfc34004672a191bb5ad791d971
Source dataset
uspto-grants-1985_09
Patent number
US04540791

Reaction notes

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