2-Butenoic acid, 3-amino-, ethyl ester, (2Z)- → 3-Methyl 5-ethyl 4-(2-chlorophenyl)-2-{[2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)ethoxy]methyl}-6-methyl-1,4-dihydro-3,5-pyridine dicarboxylate

87 g of methyl 2-(o-chlorobenzylidene)-4-(2-phthalimidoethoxy)acetoacetate was dissolved in 102 ml of 2-propanol at 80° C. 33.1 g of ethyl-3-aminocrotonate was added and the mixture was heated at the same temperature for 16 hours. The mixture was evaporated to dryness. The residue was dissolved in 153 ml of glacial acetic acid at 80° C. The mixture was cooled to 15° C. and stirred at the same temperature for 20 hours. The solid was filtered off and washed with 78 ml of glacial acetic acid. The solid was suspended in 150 ml of methanol and agitated at 60° C. for 30 minutes. The solid was cooled to 20° C. and filtered off, washed with 30 ml of methanol and dried. The product was recrystallized from ethyl acetate.

1. temperaturethe mixture was heated at the same temperature for 16 hours
2. customThe mixture was evaporated to dryness
3. dissolutionThe residue was dissolved in 153 ml of glacial acetic acid at 80° C
4. filtrationThe solid was filtered off
5. washwashed with 78 ml of glacial acetic acid
6. stirringagitated at 60° C. for 30 minutes
7. temperatureThe solid was cooled to 20° C.
8. filtrationfiltered off
9. washwashed with 30 ml of methanol
10. customdried
11. customThe product was recrystallized from ethyl acetate

ORD record

ord-249d482791444153aaceda86e7b6522a

Source dataset

uspto-grants-2005_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06858738B2