1,2-Dichlorobenzene → HCID 23078374, compound

HRID 228873Notes

Reaction equation

[OH:1][C:2]1[C:3](I)=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][CH:6]=[CH:5]2.Cl[C:14]1[C:23]2[C:18](=[CH:19][C:20]([O:26][CH3:27])=[C:21]([O:24][CH3:25])[CH:22]=2)[N:17]=[CH:16][CH:15]=1.[Cl:28]C1C=CC=CC=1Cl>CN(C)C1C=CN=CC=1>[Cl:28][C:3]1[C:2]([O:1][C:14]2[C:23]3[C:18](=[CH:19][C:20]([O:26][CH3:27])=[C:21]([O:24][CH3:25])[CH:22]=3)[N:17]=[CH:16][CH:15]=2)=[CH:11][CH:10]=[C:9]2[C:4]=1[CH:5]=[CH:6][CH:7]=[N:8]2

Participants

Conditions

Temperature: 120 °C

Procedure

6-Hydroxy-5-iodo-quinoline (100 mg), 4-chloro-6,7-dimethoxyquinoline (215 mg), and 4-dimethylaminopyridine (367 mg) were suspended in o-dichlorobenzene (12 ml), and the suspension was stirred at 120° C. for 5 hr. The reaction solution was cooled to room temperature, and the solvent was removed by distillation under the reduced pressure. Water was then added to the residue, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was then washed with water and was dried over anhydrous sodium sulfate. The solvent was removed by distillation under the reduced pressure, and the residue was purified by thin layer chromatography using acetone-chloroform to give the title compound (20 mg, yield 12%).

Workup

temperatureThe reaction solution was cooled to room temperature
customthe solvent was removed by distillation under the reduced pressure
additionWater was then added to the residue
extractionthe mixture was extracted with ethyl acetate
washThe ethyl acetate layer was then washed with water
dry with materialwas dried over anhydrous sodium sulfate
customThe solvent was removed by distillation under the reduced pressure
customthe residue was purified by thin layer chromatography

Sources & evidence

ORD record: ord-296d633d444b4a2aa49373fc397fe381
Source dataset: uspto-grants-2009_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07560558B2

Reaction notes

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