Hexane → HCID 22466619, compound

HRID 612122Notes

Reaction equation

HRID 612122 reaction equation
[C:1]1(=[O:8])[O:7][C:5](=[O:6])[CH2:4][C:2]1=[CH2:3].[NH2:9][C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][CH:19]=1)[N:16]=[CH:15][C:14]([C:20]#[N:21])=[C:13]2[NH:22][C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([Br:29])[CH:24]=1.CCCCCC>C(OCC)(=O)C>[Br:29][C:25]1[CH:24]=[C:23]([NH:22][C:13]2[C:12]3[C:17](=[CH:18][CH:19]=[C:10]([NH:9][C:5](=[O:6])[CH2:4][C:2](=[CH2:3])[C:1]([OH:7])=[O:8])[CH:11]=3)[N:16]=[CH:15][C:14]=2[C:20]#[N:21])[CH:28]=[CH:27][CH:26]=1

Participants

5

Reactant 3

HCID 8058HexaneHCID 75110Itaconic AnhydrideHCID 99677126-Amino-4-(3-bromophenylamino)quinoline-3-carbonitrile

Product 1

HCID 22466619HCID 22466619, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Itaconic anhydride (0.14 g, 1.25 mmol) was added portionwise to a solution of 0.1 g (0.30 mmol) of 6-amino-4-[(3-bromophenyl)amino]-3-quinolinecarbonitrile in 2 mL of ethyl acetate under N2. After stirring at room temperature overnight, the reaction solution was added into ice water and hexane. The product was collected, washed with water, ether and hexane, and dried in vacuo to give 0.09 g (68%) of yellowish brown solid; ESMS m/z 451.2 (M+H+).

Workup

  1. customThe product was collected
  2. washwashed with water, ether and hexane
  3. customdried in vacuo

Sources & evidence

ORD record
ord-2a16a2c1928c427d91a9aa24d32855f1
Source dataset
uspto-grants-1999_12
Patent number
US06002008

Reaction notes

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