Sodium Carbonate → 2-[3-Bis(2-hydroxyethyl)aminopropyl]amino-quinoline

HRID 258815Notes

Reaction equation

HRID 258815 reaction equation
Cl[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N: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>[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[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 119282-ChloroquinolineHCID 21088(3-Aminopropyl)diethanolamine

Product 1

HCID 214246762-[3-Bis(2-hydroxyethyl)aminopropyl]amino-quinoline

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of 5.05 g. of 2-chloroquinoline, 5.5 g. of bis(2-hydroxyethyl)aminopropylamine and 3.0 g. of sodium carbonate is heated in 20 ml. of refluxing isopropanol for 24 hours. The reaction mixture is then filtered, solvent removed in vacuo and the residue chromatographed over silica gel to obtain an oil of 2-[3-bis(2-hydroxyethyl)aminopropyl]amino-quinoline.

Workup

  1. additionA mixture of 5.05 g
  2. filtrationThe reaction mixture is then filtered
  3. customsolvent removed in vacuo
  4. customthe residue chromatographed over silica gel

Sources & evidence

ORD record
ord-03178fbcc19d4bcd8274cb500c301743
Source dataset
uspto-grants-1977_07
Patent number
US04035367

Reaction notes

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