Ethanolamine → 2-[(7-chloroquinolin-4-yl)amino]ethanol

HRID 550878Notes

Reaction equation

HRID 550878 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([Cl:12])=[CH:9][CH:10]=2)[N:5]=[CH:4][CH:3]=1.[NH2:13][CH2:14][CH2:15][OH:16].[OH-].[Na+]>>[Cl:12][C:8]1[CH:7]=[C:6]2[C:11]([C:2]([NH:13][CH2:14][CH2:15][OH:16])=[CH:3][CH:4]=[N:5]2)=[CH:10][CH:9]=1

Participants

4

Reactant 3

HCID 700EthanolamineHCID 68664,7-DichloroquinolineHCID 14798Sodium Hydroxide

Product 1

HCID 46504662-[(7-chloroquinolin-4-yl)amino]ethanolYield 93%

Procedure

A mixture of 4,7-dichloroquinoline (50.0 g, 252 mmol) and of 2-aminoethanol (46.26 g, 757 mmol) is heated, with magnetic stirring, at 150° C. for 15 min and then at 185° C. for 30 min. After returning to ambient temperature, the solid is suspended in 250 ml of a 10%, w/v, aqueous sodium hydroxide solution. The precipitate obtained is filtered off through sintered glass, washed with water and then brought to reflux in 125 ml of methanol for 15 min. After returning to ambient temperature, the precipitate is filtered off through sintered glass, washed with 3 times 40 ml of methanol and then dried under vacuum. The product 5 is obtained in the form of a white powder: 52.28 g (yield=93%).

Workup

  1. customAfter returning to ambient temperature
  2. customThe precipitate obtained
  3. filtrationis filtered off through sintered glass
  4. washwashed with water
  5. temperatureto reflux in 125 ml of methanol for 15 min
  6. customAfter returning to ambient temperature
  7. filtrationthe precipitate is filtered off through sintered glass
  8. washwashed with 3 times 40 ml of methanol
  9. customdried under vacuum

Sources & evidence

ORD record
ord-8d037479bd444f789d4d96052da44344
Source dataset
uspto-grants-2011_05
Patent number
US07947701B2

Reaction notes

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