Ethanolamine → 6-Dimethylamino-4-(beta-hydroxyethylamino)quinoline

HRID 550884Notes

Reaction equation

HRID 550884 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([N:12]([CH3:14])[CH3:13])[CH:10]=2)[N:5]=[CH:4][CH:3]=1.[NH2:15][CH2:16][CH2:17][OH:18].[OH-].[Na+]>O>[CH3:13][N:12]([CH3:14])[C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][CH:8]=1)[N:5]=[CH:4][CH:3]=[C:2]2[NH:15][CH2:16][CH2:17][OH:18]

Participants

5

Reactant 3

HCID 700EthanolamineHCID 14798Sodium HydroxideHCID 436172264-chloro-N,N-dimethylquinolin-6-amine

Product 1

HCID 671895216-Dimethylamino-4-(beta-hydroxyethylamino)quinolineYield 88%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 4-chloro-6-dimethylaminoquinoline 12 (4.92 g, 24 mmol), prepared according to the method described by Riegel et al., J. Am. Chem. Soc., 1946, 68, 1264, and of 2-aminoethanol (43.99 g, 720 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 25 ml of a 10%, w/v, aqueous sodium hydroxide solution and 165 ml of water. The precipitate obtained is filtered through sintered glass, washed with water and then dried under vacuum. The product is obtained in the form of a white powder: 4.86 g (yield=88%).

Workup

  1. customprepared
  2. customAfter returning to ambient temperature
  3. customThe precipitate obtained
  4. filtrationis filtered through sintered glass
  5. washwashed with water
  6. customdried under vacuum
  7. customThe product is obtained in the form of a white powder

Sources & evidence

ORD record
ord-1e26f6f577354dbba12349ce537f700b
Source dataset
uspto-grants-2011_05
Patent number
US07947701B2

Reaction notes

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