4,7-Dichloroquinoline → 1-Propanol, 3-[(7-chloro-4-quinolinyl)amino]-

HRID 244387Notes

Reaction equation

HRID 244387 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][CH2:16][OH:17]>O>[Cl:12][C:8]1[CH:7]=[C:6]2[C:11]([C:2]([NH:13][CH2:14][CH2:15][CH2:16][OH:17])=[CH:3][CH:4]=[N:5]2)=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 68664,7-DichloroquinolineHCID 90863-Amino-1-propanol

Product 1

HCID 3709951-Propanol, 3-[(7-chloro-4-quinolinyl)amino]-Yield 90.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
135 °C

Procedure

A mixture of 4,7-dichloroquinoline (25.35 g, 0.128 mol) and 3-aminopropanol (120 mL, 1.57 mol) were heated with stirring at 130-140° C. for 24 hours. After cooling, the reaction mixture was poured into water (500 mL) and filtered, and the solid residue was dried then boiled in ethyl acetate (250 mL) to give the title compound (27.3 g, 90%) as an off-white solid.

Workup

  1. temperaturewere heated
  2. temperatureAfter cooling
  3. filtrationfiltered
  4. customthe solid residue was dried

Sources & evidence

ORD record
ord-fc6bfc11c84547f1b52be2d6177a1fb4
Source dataset
uspto-grants-2014_02
Patent number
US08658648B2

Reaction notes

Loading…