Ethanolamine → 2-((7-(Trifluoromethyl)quinolin-4-yl)amino)ethanol

HRID 550881Notes

Reaction equation

HRID 550881 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12]([F:15])([F:14])[F:13])=[CH:9][CH:10]=2)[N:5]=[CH:4][CH:3]=1.[NH2:16][CH2:17][CH2:18][OH:19].[OH-].[Na+]>>[F:13][C:12]([F:15])([F:14])[C:8]1[CH:7]=[C:6]2[C:11]([C:2]([NH:16][CH2:17][CH2:18][OH:19])=[CH:3][CH:4]=[N:5]2)=[CH:10][CH:9]=1

Participants

4

Reactant 3

HCID 700EthanolamineHCID 14798Sodium HydroxideHCID 676684-Chloro-7-(trifluoromethyl)quinoline

Product 1

HCID 671877912-((7-(Trifluoromethyl)quinolin-4-yl)amino)ethanolYield 68%

Procedure

A mixture of 4-chloro-7-(trifluoromethyl)quinoline (1.0 g, 4.7 mmol) and of 2-aminoethanol (0.86 g, 14.1 mmol) is heated, with magnetic stirring, at 150° C. for 15 min and then 185° C. for 30 min. After returning to ambient temperature, the solid is suspended in 5 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 10 ml of ethanol for 15 min. After returning to ambient temperature, water is added until a precipitate appears. The precipitate is filtered off through sintered glass, washed with 10 ml of water and then dried under vacuum. The product 10 is obtained in the form of a white powder: 0.82 g (yield=68%). Mp: 181-182° C.

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 10 ml of ethanol for 15 min
  6. customAfter returning to ambient temperature
  7. additionwater is added until a precipitate
  8. filtrationThe precipitate is filtered off through sintered glass
  9. washwashed with 10 ml of water
  10. customdried under vacuum

Sources & evidence

ORD record
ord-1d38d98f1d134d54ab37964242f916e8
Source dataset
uspto-grants-2011_05
Patent number
US07947701B2

Reaction notes

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