Propanoic acid, 3-ethoxy-3-imino-, ethyl ester → 3-Ethoxy-3-(3-methoxy-2-methyl-phenylimino)-propionic acid ethyl ester

HRID 1893669Notes

Reaction equation

HRID 1893669 reaction equation
[CH3:1][O:2][C:3]1[C:4]([CH3:10])=[C:5]([CH:7]=[CH:8][CH:9]=1)[NH2:6].[CH2:11]([O:13][C:14](=N)[CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH3:12]>CCO>[CH2:19]([O:18][C:16](=[O:17])[CH2:15][C:14]([O:13][CH2:11][CH3:12])=[N:6][C:5]1[CH:7]=[CH:8][CH:9]=[C:3]([O:2][CH3:1])[C:4]=1[CH3:10])[CH3:20]

Participants

4

Reactant 2

HCID 75346Propanoic acid, 3-ethoxy-3-imino-, ethyl esterHCID 118048223-Methoxy-2-methylaniline

Product 1

HCID 576034223-Ethoxy-3-(3-methoxy-2-methyl-phenylimino)-propionic acid ethyl esterYield 88.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 3-methoxy-2-methylaniline (2.15 g, 15.6 mmol) in anhydrous EtOH (30 mL) was added ethyl 3-ethoxy-3-imino-propionate (3.05 g, 15.6 mmol). The reaction was stirred overnight then filtered through celite. The filtrate was concentrated then purified by column chromatography on silica (2→10% EtOAc/hexane) to afford 3-ethoxy-3-(3-methoxy-2-methyl-phenylimino)-propionic acid ethyl ester (3.84 g, 88%). LCMS found 280.2 [M+H]+.

Workup

  1. filtrationthen filtered through celite
  2. concentrationThe filtrate was concentrated
  3. customthen purified by column chromatography on silica (2→10% EtOAc/hexane)

Sources & evidence

ORD record
ord-8baf37b7ebec4936b141fded9f969208
Source dataset
uspto-grants-2013_08
Patent number
US08513186B2

Reaction notes

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