Propanedioic acid, 2-amino-, 1,3-diethyl ester, hydrochloride (1:1) → [(5-Chloro-2-hydroxy-alpha-phenylbenzyliden)amino] malonic acid diethyl ester
Reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:16])=[C:6]([CH:15]=1)[C:7](=[NH:14])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.Cl.[CH2:18]([O:20][C:21](=[O:29])[CH:22](N)[C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH3:19]>N1C=CC=CC=1>[CH2:18]([O:20][C:21](=[O:29])[CH:22]([N:14]=[C:7]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:6]1[CH:15]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=1[OH:16])[C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH3:19]Participants
Procedure
A suspension of 9.2 g. of 5-chloro-2-hydroxy-benzophenone imine in 60 ml. of ehtanol is treated with 12.6 g. of aminomalonic acid diethyl ester hyrochloride and 5.0 ml. of pyridine and the mixture boiled at reflux for 1 hour while stirring. The mixture is then concentrated to dryness under reduced pressure and the residue partitioned between toluene and water. The organic phase is washed with water, briefly dried over sodium sulfate and evaporated to dryness. The residual oily residue crystallizes upon trituration with hexane. There is obtained [(5-chloro-2-hydroxy-α-phenylbenzyliden)amino] malonic acid diethyl ester, having a melting point of 55°-56° C. Recrystallization from ethanol yields gold-yellowish leaflets having the same melting point.
Workup
- additionA suspension of 9.2 g
- additionof ehtanol is treated with 12.6 g
- temperatureat reflux for 1 hour
- concentrationThe mixture is then concentrated to dryness under reduced pressure
- customthe residue partitioned between toluene and water
- washThe organic phase is washed with water
- dry with materialbriefly dried over sodium sulfate
- customevaporated to dryness
- customThe residual oily residue crystallizes upon trituration with hexane
Sources & evidence
- ORD record
- ord-849ad2bd07af4b0188382bd1be544090
- Source dataset
- uspto-grants-1978_05
- Patent number
- US04089875
Reaction notes
Loading…