Diethanolamine → 4-[N,N-bis(2-hydroxyethyl)amino]-2-trifluoromethylquinoline

HRID 1791945Notes

Reaction equation

[NH:1]([CH2:5][CH2:6][OH:7])[CH2:2][CH2:3][OH:4].Cl[C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[N:12]=[C:11]([C:19]([F:22])([F:21])[F:20])[CH:10]=1>[Cl-].[Na+].O>[OH:4][CH2:3][CH2:2][N:1]([C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[N:12]=[C:11]([C:19]([F:22])([F:20])[F:21])[CH:10]=1)[CH2:5][CH2:6][OH:7]

Participants

Conditions

Temperature: 80 °C

Procedure

Diethanolamine (20 mL) was added to 4-chloro-2-trifluoromethylquinoline (5.04 g), and the mixture was stirred at 80° C. for 19 hr. Brine was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was dried and concentrated under reduced pressure. The residue was purified by silica gel chromatography to give 4-[N,N-bis(2-hydroxyethyl)amino]-2-trifluoromethylquinoline (3.40 g) as a white powder.

Workup

extractionthe mixture was extracted with ethyl acetate
customThe extract was dried
concentrationconcentrated under reduced pressure
customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record: ord-4ef913eea72040918018fad2ac95998a
Source dataset: uspto-grants-2006_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07074794B2

Reaction notes

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