Hydrogen Bromide → 6-Dimethylamino-4-(beta-bromoethylamino)quinoline

HRID 550885Notes

Reaction equation

[BrH:1].S(=O)(=O)(O)O.[CH3:7][N:8]([CH3:23])[C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[N:15]=[CH:14][CH:13]=[C:12]2[NH:19][CH2:20][CH2:21]O.C([O-])(O)=O.[Na+]>O>[CH3:7][N:8]([CH3:23])[C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[N:15]=[CH:14][CH:13]=[C:12]2[NH:19][CH2:20][CH2:21][Br:1]

Participants

Conditions

Temperature: 165 °C

Procedure

Hydrobromic acid (6.6 ml, 122 mmol) and then sulphuric acid (2.2 ml, 41.4 mmol) are added dropwise to the 6-dimethylamino-4-(β-hydroxyethylamino)quinoline 13 (4.56 g, 19.7 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 71 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 (71 ml) for 15 min. The organic phase is then collected and the product is obtained by crystallization at −18° C. overnight, filtration, and then washing with hexane and drying under vacuum: 3.28 g (yield=57%).

Workup

extractionthe medium is then extracted at the
temperaturereflux of toluene (71 ml) for 15 min
customThe organic phase is then collected
customthe product is obtained by crystallization at −18° C. overnight
filtrationfiltration
washwashing with hexane
customdrying under vacuum

Sources & evidence

ORD record: ord-199d2ec0f4f443d08e2b28dcb467b8cf
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07947701B2

Reaction notes

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