Hydrochloric Acid → Diethyl methyl-(4-amino)benzylmalonate

HRID 248063Notes

Reaction equation

HRID 248063 reaction equation
[CH3:1][C:2]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([NH:20]C(=O)C)=[CH:16][CH:15]=1)([C:8]([O:10][CH2:11][CH3:12])=[O:9])[C:3]([O:5][CH2:6][CH3:7])=[O:4].Cl.C(=O)([O-])O>>[CH3:1][C:2]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([NH2:20])=[CH:16][CH:15]=1)([C:8]([O:10][CH2:11][CH3:12])=[O:9])[C:3]([O:5][CH2:6][CH3:7])=[O:4]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 769Bicarbonate IonHCID 54008305Diethyl methyl-(4-acetamido)benzylmalonate

Product 1

HCID 54055855Diethyl methyl-(4-amino)benzylmalonate

Procedure

Mix diethyl methyl-(4-acetamido)benzylmalonate (5.01 g, 15.6 mmol) and 2N hydrochloric acid (65 mL) and heat at reflux for several hours. Cool to room temperature, basify with solid hydrogen carbonate and extract into ethyl ether (3×). Dry (MgSO4) and evaporate the solvent in vacuo to give diethyl methyl-(4-amino)benzylmalonate.

Workup

  1. temperatureheat
  2. temperatureat reflux for several hours
  3. extractionextract into ethyl ether (3×)
  4. dry with materialDry (MgSO4)
  5. customevaporate the solvent in vacuo

Sources & evidence

ORD record
ord-05b0ce8b6270496ab4525a8a2b7e8ddd
Source dataset
uspto-grants-1993_05
Patent number
US05208240

Reaction notes

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