Methyl 3-aminocrotonate → Phthalimidoamlodipine

HRID 25475

Reaction equation

[Cl:1][C:2]1[CH:31]=[CH:30][CH:29]=[CH:28][C:3]=1[CH:4]=[C:5]([C:11]([CH2:13][O:14][CH2:15][CH2:16][N:17]1[C:21](=[O:22])[C:20]2=[CH:23][CH:24]=[CH:25][CH:26]=[C:19]2[C:18]1=[O:27])=O)[C:6]([O:8][CH2:9][CH3:10])=[O:7].[CH3:32][O:33][C:34](=[O:39])/[CH:35]=[C:36](\[NH2:38])/[CH3:37]>CC(O)C>[Cl:1][C:2]1[CH:31]=[CH:30][CH:29]=[CH:28][C:3]=1[CH:4]1[C:35]([C:34]([O:33][CH3:32])=[O:39])=[C:36]([CH3:37])[NH:38][C:11]([CH2:13][O:14][CH2:15][CH2:16][N:17]2[C:21](=[O:22])[C:20]3[C:19](=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:18]2=[O:27])=[C:5]1[C:6]([O:8][CH2:9][CH3:10])=[O:7]

Participants

Conditions

Temperature: 15 °C

Procedure

350 g of crude ethyl 2-(o-chlorobenzylidene)-4-(2-phthalimidoethoxy) acetoacetate from Example 1 was dissolved in 540 ml of 2-propanol at 80° C. 50 g of methyl-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 540 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 formed solid was filtered off and washed with 280 ml of glacial acetic acid. The solid was suspended in 225 ml of methanol and agitated for 30 minutes. The solid was filtered off, washed with 75 ml of methanol and dried.

Workup

temperaturethe mixture was heated at the same temperature for 16 hours
customThe mixture was evaporated to dryness
dissolutionThe residue was dissolved in 540 ml of glacial acetic acid at 80° C
filtrationThe formed solid was filtered off
washwashed with 280 ml of glacial acetic acid
stirringagitated for 30 minutes
filtrationThe solid was filtered off
washwashed with 75 ml of methanol
customdried

Sources & evidence

ORD record: ord-373b8316f2424a3bbbfd26a259af20b1
Source dataset: uspto-grants-2005_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06858738B2

Linked notes

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