Water → 8-(2,6-Dichlorobenzoylamino)-4-(2-methoxyethylamino)quinoline

HRID 613482Notes

Reaction equation

Cl[C:2]1[C:11]2[C:6](=[C:7]([NH:12][C:13](=[O:22])[C:14]3[C:19]([Cl:20])=[CH:18][CH:17]=[CH:16][C:15]=3[Cl:21])[CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][CH:3]=1.[CH3:23][O:24][CH2:25][CH2:26][NH2:27].O>CN1CCCC1=O>[Cl:21][C:15]1[CH:16]=[CH:17][CH:18]=[C:19]([Cl:20])[C:14]=1[C:13]([NH:12][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:6]=1[N:5]=[CH:4][CH:3]=[C:2]2[NH:27][CH2:26][CH2:25][O:24][CH3:23])=[O:22]

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of 4-chloro-8-(2,6-dichlorobenzoylamino)quinoline (100 mg) and 2-methoxyethylamine (314 mg) in N-methylpyrrolidone (1 ml) was heated at 120° C. overnight. Water (3 ml) was added thereto under ice-cooling, and the mixture was stirred for 1 hour. The resulting precipitate was collected by filtration, and the residue was purified by preparative thin layer chromatography (methanoldichloromethane) to give 8-(2,6-dichlorobenzoylamino)-4-(2-methoxyethylamino)quinoline (65 mg).

Workup

temperatureunder ice-cooling
filtrationThe resulting precipitate was collected by filtration
customthe residue was purified by preparative thin layer chromatography (methanoldichloromethane)

Sources & evidence

ORD record: ord-dc6e75d722ca4b0c8756d753ca37e306
Source dataset: uspto-grants-1999_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06008230

Reaction notes

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