Methanol → 1-methyl-6-[3-(quinolin-6-ylamino)propoxy]-1H-quinolin-2-one

HRID 1504202Notes

Reaction equation

[NH2:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][CH:6]=[CH:5]2.CO.I[CH2:15][CH2:16][CH2:17][O:18][C:19]1[CH:20]=[C:21]2[C:26](=[CH:27][CH:28]=1)[N:25]([CH3:29])[C:24](=[O:30])[CH:23]=[CH:22]2>ClCCl>[CH3:29][N:25]1[C:26]2[C:21](=[CH:20][C:19]([O:18][CH2:17][CH2:16][CH2:15][NH:1][C:2]3[CH:3]=[C:4]4[C:9](=[CH:10][CH:11]=3)[N:8]=[CH:7][CH:6]=[CH:5]4)=[CH:28][CH:27]=2)[CH:22]=[CH:23][C:24]1=[O:30]

Participants

Conditions

Temperature: 60 °C

Procedure

6-Aminoquinoline(360 mg) was added to the methanol solution(10 ml) of 6-(3-iodopropoxy)-1-methyl-1H-quinolin-2-one(172 mg) and stirred at 60° C. for 17 hours. The reaction mixture was added to ice water, and extraction with dichloromethane was performed. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate: methanol=10:0→4:1). The purified product was condensed under reduced pressure to give the title compound(86.4 mg) as a yellow amorphous solid.

Workup

dry with materialThe organic layer was dried over anhydrous sodium sulfate
concentrationconcentrated under reduced pressure
customThe residue was purified by silica gel column chromatography (ethyl acetate: methanol=10:0→4:1)
customcondensed under reduced pressure

Sources & evidence

ORD record: ord-407ad6b5484b43eba21dcedd0c932c71
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09212187B2

Reaction notes

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