Isopropanol → 4-[3-Bis(2-hydroxyethyl)aminopropyl]amino-quinoline

HRID 1076642Notes

Reaction equation

HRID 1076642 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][CH:3]=1.[OH:12][CH2:13][CH2:14][N:15]([CH2:19][CH2:20][CH2:21][NH2:22])[CH2:16][CH2:17][OH:18].C(=O)([O-])[O-].[Na+].[Na+].C(O)(C)C>C(Cl)(Cl)Cl>[OH:18][CH2:17][CH2:16][N:15]([CH2:14][CH2:13][OH:12])[CH2:19][CH2:20][CH2:21][NH:22][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 3776IsopropanolHCID 10340Sodium CarbonateHCID 21088(3-Aminopropyl)diethanolamineHCID 691404-Chloroquinoline

Product 1

HCID 214246874-[3-Bis(2-hydroxyethyl)aminopropyl]amino-quinoline

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of 5.0 g. of 4-chloroquinoline, 7.2 g. of bis(2-hydroxyethyl)aminopropylamine, 3.0 g. of sodium carbonate and 25 ml. of isopropanol is heated in a pressure vessel at 150°C. for 17 hours. The resulting mixture is diluted with chloroform, filtered and purified by filtering over silica gel to obtain an oil of 4-[3-bis(2-hydroxyethyl)aminopropyl]amino-quinoline.

Workup

  1. additionA mixture of 5.0 g
  2. filtrationfiltered
  3. custompurified
  4. filtrationby filtering over silica gel

Sources & evidence

ORD record
ord-2f09f7d6480c4d7b9cec6cfcddc92c89
Source dataset
uspto-grants-1976_05
Patent number
US03957791

Reaction notes

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