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

HRID 612016Notes

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(N(CC)CC)C.[C:30](Cl)(=[O:33])[CH:31]=[CH2:32]>O1CCCC1>[Br:22][C:17]1[CH:16]=[C:15]([NH:14][C:5]2[C:4]3[C:9](=[CH:10][CH:11]=[C:2]([NH:1][C:30](=[O:33])[CH:31]=[CH2:32])[CH:3]=3)[N:8]=[CH:7][C:6]=2[C:12]#[N:13])[CH:20]=[CH:19][C:18]=1[Br:21]

Participants

Conditions

Temperature: 25 °C

Procedure

To a solution of 0.75 g (1.79 mmol) of 6-amino-4-[(3,4-dibromophenyl)amino]-3-quinolinecarbonitrile and 0.22 g (2.15 mmol) of triethylamine in 10 mL of tetrahydrofuran was added dropwise 0.195 g (2.15 mmol) of acryloyl chloride. After stirring overnight at 25° C., volatile material was removed and the residue was slurried in water and solid was collected. The crude product was washed with boiling ethyl acetate dried in vacuo (50° C.) to give 0.609 g of brown solid: high resolution mass spectrum (m/e): 470.9457.

Workup

customvolatile material was removed
customsolid was collected
washThe crude product was washed with boiling ethyl acetate
customdried in vacuo (50° C.)

Sources & evidence

ORD record: ord-da21e736817140b29b3e45a247f02db3
Source dataset: uspto-grants-1999_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06002008

Reaction notes

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