Propylamine → ethyl (2Z)-3-(2-chloropyridin-3-yl)-2-cyano-3-(propylamino)acrylate

HRID 444695Notes

Reaction equation

Cl[C:2]([C:11]1[C:12]([Cl:17])=[N:13][CH:14]=[CH:15][CH:16]=1)=[C:3]([C:9]#[N:10])[C:4]([O:6][CH2:7][CH3:8])=[O:5].[CH2:18]([NH2:21])[CH2:19][CH3:20]>O1CCCC1>[Cl:17][C:12]1[C:11](/[C:2](/[NH:21][CH2:18][CH2:19][CH3:20])=[C:3](\[C:9]#[N:10])/[C:4]([O:6][CH2:7][CH3:8])=[O:5])=[CH:16][CH:15]=[CH:14][N:13]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of ethyl 3-chloro-3-(2-chloropyridin-3-yl)-2-cyanoacrylate (0.3 g, 1.10 mmol, 1 eq.) in 5 ml of tetrahydrofuran was added propylamine (0.131 g, 2.21 mmol, 2 eq.) at room temperature. After being stirred for 8 h at 80° C., the mixture was evaporated. The residue was diluted with AcOEt and the precipitate was filtered off. The filtrate was evaporated and the residual oil was subjected to column chromatography to give ethyl (2Z)-3-(2-chloropyridin-3-yl)-2-cyano-3-(propylamino)acrylate (0.240 g, 74% yield).

Workup

customthe mixture was evaporated
additionThe residue was diluted with AcOEt
filtrationthe precipitate was filtered off
customThe filtrate was evaporated

Sources & evidence

ORD record: ord-e5f3d28943ad4489abf51a9845c02846
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08476197B2

Reaction notes

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