Hydrogen Bromide → 7-Trifluoromethyl-4-(beta-bromoethylamino)quinoline

HRID 550882Notes

Reaction equation

[BrH:1].S(=O)(=O)(O)O.[F:7][C:8]([F:24])([F:23])[C:9]1[CH:18]=[C:17]2[C:12]([C:13]([NH:19][CH2:20][CH2:21]O)=[CH:14][CH:15]=[N:16]2)=[CH:11][CH:10]=1.C([O-])(O)=O.[Na+]>O>[F:7][C:8]([F:24])([F:23])[C:9]1[CH:18]=[C:17]2[C:12]([C:13]([NH:19][CH2:20][CH2:21][Br:1])=[CH:14][CH:15]=[N:16]2)=[CH:11][CH:10]=1

Participants

Conditions

Temperature: 165 °C

Procedure

Hydrobromic acid (0.88 ml, 16.2 mmol) and then sulphuric acid (0.29 ml, 5.5 mmol) are added dropwise to the 7-trifluoromethyl-4-(β-hydroxyethylamino)quinoline 10 (0.67 g, 2.6 mmol), the reaction medium being refrigerated using a bath of cold water. The reaction medium is then heated at 165° C. for 3 h 30 min, and then poured into 10 ml of cold water. The pH is then adjusted by adding NaHCO3 (pH approximately 9) and the medium is then extracted at the reflux of toluene (10 ml) for 15 min. The organic phase is then collected and the product 11 is obtained by crystallization at −18° C. overnight, filtration, and then drying under vacuum: 0.48 g (yield=58%). Mp: 106° C. (decomp.).

Workup

extractionthe medium is then extracted at the
temperaturereflux of toluene (10 ml) for 15 min
customThe organic phase is then collected

Sources & evidence

ORD record: ord-cff83e05c5c6482ab78021e4add0cbd7
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07947701B2

Reaction notes

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