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

HRID 1829154Notes

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-5a12686d5b184c17957184f36a38ae38
Source dataset: uspto-grants-2006_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07060722B2

Reaction notes

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