Sodium Bicarbonate → 6-Amino-4-(3,4-dibromophenylamino)quinoline-3-carbonitrile

HRID 379110

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[C:19]3[C:14](=[CH:15][CH:16]=[C:17]([N+:20]([O-])=O)[CH:18]=3)[N:13]=[CH:12][C:11]=2[C:23]#[N:24])[CH:5]=[CH:6][C:7]=1[Br:8].C(=O)(O)[O-].[Na+]>C(O)C>[NH2:20][C:17]1[CH:18]=[C:19]2[C:14](=[CH:15][CH:16]=1)[N:13]=[CH:12][C:11]([C:23]#[N:24])=[C:10]2[NH:9][C:4]1[CH:5]=[CH:6][C:7]([Br:8])=[C:2]([Br:1])[CH:3]=1

Participants

Conditions

Temperature: 25 °C

Procedure

A mixture of 4.90 g (10.9 mmol) of 4-[(3,4-dibromophenyl)amino]-6-nitro-quinoline-3-carbonitrile and 12.4 g (54.7 mmol) of SnCl2 dihydrate in 200 mL of ethanol was refluxed under N2 for 1.5 h. After cooling to 25° C., the reaction was diluted with ice water, neutralized with sodium bicarbonate and stirred for 2 h. This solution was then extracted with chloroform, treated with Darco, dried(magnesium sulfate) and evaporated. After drying in vacuo (40° C.), there was obtained 1.25 g of brown solid: mass spectrum (electrospray, m/e): M+H 417, 419, 421.

Workup

temperaturewas refluxed under N2 for 1.5 h
extractionThis solution was then extracted with chloroform
additiontreated with Darco, dried(magnesium sulfate)
customevaporated
customAfter drying in vacuo (40° C.)

Sources & evidence

ORD record: ord-7f9acf51c657454f84c787e13f244049
Source dataset: uspto-grants-2001_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06297258B1

Linked notes

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