Acryloyl chloride → N-[3-cyano-4-(3,4-dibromophenylamino)quinolin-6-yl]acrylamide

HRID 612264Notes

Reaction equation

[NH2:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][C:6]([C:12]#[N:13])=[C:5]2[NH:14][C:15]1[CH:20]=[CH:19][C:18]([Br:21])=[C:17]([Br:22])[CH:16]=1.[C:23](Cl)(=[O:26])[CH:24]=[CH2:25]>C1COCC1>[C:12]([C:6]1[CH:7]=[N:8][C:9]2[C:4]([C:5]=1[NH:14][C:15]1[CH:20]=[CH:19][C:18]([Br:21])=[C:17]([Br:22])[CH:16]=1)=[CH:3][C:2]([NH:1][C:23](=[O:26])[CH:24]=[CH2:25])=[CH:11][CH:10]=2)#[N:13]

Participants

Conditions

Temperature: 25 °C

Procedure

6-Amino-4-(3,4-dibromophenylamino)quinoline-3-carbonitrile (0.750 g. 1.79 mmol) in mL of THF was treated with 0.217 g (2.15 mmol) of EtN and 0.195 g (2.15 mmol) of acryloyl chloride at 0° C. under N2. After stirring overnight at 25° C., the solvent was evaporated and the residue was slurried with water and collected. The residue was boiled twice with EtOAc and then dried in vacuo (50° C.) to give 0.609 g of N-[3-cyano-4-(3,4-dibromophenylamino)quinolin-6-yl]acrylamide as a brown solid: mass spectrum (electrospray, m/e): 470.9, 472.9.

Workup

customthe solvent was evaporated
customcollected
customdried in vacuo (50° C.)

Sources & evidence

ORD record: ord-95b9f5d9c14d4bf9909bd8d009582a97
Source dataset: uspto-grants-1999_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06002008

Reaction notes

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