Hydrogen Bromide → HCID 15965578, compound

HRID 550879Notes

Reaction equation

HRID 550879 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)=[CH:13][CH:14]=[N:15]2)=[CH:10][CH:9]=1.C([O-])(O)=O.[Na+]>O>[Cl:7][C:8]1[CH:17]=[C:16]2[C:11]([C:12]([NH:18][CH2:19][CH2:20][Br:1])=[CH:13][CH:14]=[N:15]2)=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 260Hydrogen BromideHCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 46504662-[(7-chloroquinolin-4-yl)amino]ethanol

Product 1

HCID 15965578HCID 15965578, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
165 °C

Procedure

Hydrobromic acid (22.5 ml, 414 mmol) and then sulphuric acid (7.5 ml, 140 mmol) are added dropwise onto the 7-chloro-4-(β-hydroxyethylamino)quinoline 5 (15 g, 67 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 300 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 (300 ml) for 15 min. The organic phase is then collected and the product 6 is obtained by crystallization at −18° C. overnight, filtration, and then drying under vacuum: 10.55 g (yield=55%).

Workup

  1. extractionthe medium is then extracted at the
  2. temperaturereflux of toluene (300 ml) for 15 min
  3. customThe organic phase is then collected

Sources & evidence

ORD record
ord-042f0e0eb00a414f823e28840b9d02be
Source dataset
uspto-grants-2011_05
Patent number
US07947701B2

Reaction notes

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