2-Methoxyaniline → o-[2-Ethoxycarbonyl-2-(3-ethoxycarbonylpropionyl)-1-ethylideneamino]anisole
Reaction equation
[CH3:1][O:2][C:3]1[C:4]([NH2:9])=[CH:5][CH:6]=[CH:7][CH:8]=1.[CH2:10]([O:12][C:13](=[O:24])[CH2:14][C:15](=[O:23])[CH2:16][CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH3:11].[CH:25](OCC)(OCC)OCC>C(O)C>[CH2:10]([O:12][C:13]([CH:14]([C:15](=[O:23])[CH2:16][CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH:25]=[N:9][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=1[O:2][CH3:1])=[O:24])[CH3:11]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 20 °C
Procedure
A mixture consisting of 5.0 g (0.041 mole) of o-anisidine (available from the Aldrich Chemical Company, Inc. of Milwaukee, Wis.), 8.86 g (0.041 mole) of β-ketoadipic acid diethyl ester (available from Sigma Chemical Company of St. Louis, Mo.) and 6.07 g (0.041 mole) of triethyl orthoformate (also available from Aldrich) was placed in an open reaction flask and heated to 140° C. for a period of three hours, at which point no further amount of ethanol by-product formation could be observed to evolve from the reaction mixture. Upon completion of this step, the spent reaction mixture was allowed to cool to ambient temperatures (ca. 20° C.) on standing overnight for a period of approximately 16 hours. The resulting residual solid was thereafter triturated with petroleum ether and filtered to give 11.53 g (82%) of pure o-[2-ethoxycarbonyl-2-(3-ethoxycarbonylpropionyl)-1-ethylideneamino]anisole. The pure product was characterized by means of mass spectrum (MS) analysis and nuclear magnetic resonance (NMR) data.
Workup
- customUpon completion of this step, the spent reaction mixture
- customThe resulting residual solid was thereafter triturated with petroleum ether
- filtrationfiltered
Sources & evidence
- ORD record
- ord-b8da32933a734eab98d21aeccba739b2
- Source dataset
- uspto-grants-1994_11
- Patent number
- US05362743
Reaction notes
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