Succinimide → 4-Chloro-7-((2,5-dioxopyrrolidin-1-yl)methyl)quinoline-2-carbonitrile

HRID 922756Notes

Reaction equation

[C:1]1(=[O:7])[NH:5][C:4](=[O:6])[CH2:3][CH2:2]1.CCN(C(C)C)C(C)C.Br[CH2:18][C:19]1[CH:28]=[C:27]2[C:22]([C:23]([Cl:31])=[CH:24][C:25]([C:29]#[N:30])=[N:26]2)=[CH:21][CH:20]=1>C(#N)C>[Cl:31][C:23]1[C:22]2[C:27](=[CH:28][C:19]([CH2:18][N:5]3[C:4](=[O:6])[CH2:3][CH2:2][C:1]3=[O:7])=[CH:20][CH:21]=2)[N:26]=[C:25]([C:29]#[N:30])[CH:24]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a room temperature solution of succinimide (4.22 g, 42.6 mmol, 1.2 equiv.) in anhydrous acetonitrile (89 mL, 0.4 M) was added Hunig's base (12.4 ml, 71.0 mmol, 2.0 equiv.) and 7-(bromomethyl)-4-chloroquinoline-2-carbonitrile (2-4, 10.0 g, 35.5 mmol). The resulting mixture was warmed in the microwave to 100° C. for 1 h. The reaction was then cooled to 0° C. and a precipitate formed. The solids were then collected by vacuum filtration and washed with cold acetonitrile to afford 4-chloro-7-[(2,5-dioxopyrrolidin-1-yl)methyl]quinoline-2-carbonitrile (2-5) which was taken to the next step without further purification. LRMS m/z (M+H)+ 300.2. found, 300.0 required.

Workup

temperatureThe reaction was then cooled to 0° C.
customa precipitate formed
filtrationThe solids were then collected by vacuum filtration
washwashed with cold acetonitrile

Sources & evidence

ORD record: ord-fd6dc5629760494a99c02c6c927e6ed8
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09278960B2

Reaction notes

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