Hydrogen Bromide → [2-(2-Bromoethoxy)ethyl]-(7-chloroquinolin-4-yl)amine

HRID 550887Notes

Reaction equation

[BrH:1].S(=O)(=O)(O)O.[Cl:7][C:8]1[CH:17]=[C:16]2[C:11]([C:12]([NH:18][CH2:19][CH2:20][O:21][CH2:22][CH2:23]O)=[CH:13][CH:14]=[N:15]2)=[CH:10][CH:9]=1.C([O-])(O)=O.[Na+]>O>[Br:1][CH2:23][CH2:22][O:21][CH2:20][CH2:19][NH:18][C:12]1[C:11]2[C:16](=[CH:17][C:8]([Cl:7])=[CH:9][CH:10]=2)[N:15]=[CH:14][CH:13]=1

Participants

Conditions

Temperature: 155 °C

Procedure

Hydrobromic acid (5.9 ml, 109.1 mmol) and then sulphuric acid (2.0 ml, 37.0 mmol) are added dropwise to 4.7 g of compound 21 (17.6 mmol), the reaction medium being refrigerated using a bath of cold water. The reaction medium is then heated at 155° C. for 2 h 30 min, and then poured into 70 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 (70 ml) for 20 min. The organic phase is then collected and the compound 22 is obtained after crystallization at −18° C. overnight, filtration, washing with hexane, and then drying under vacuum: 1.77 g (yield=31%).

Workup

extractionthe medium is then extracted at the
temperaturereflux of toluene (70 ml) for 20 min
customThe organic phase is then collected

Sources & evidence

ORD record: ord-3c3c8de9b9964bd393066ef0795e29ac
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07947701B2

Reaction notes

Loading…