Water → HCID 14209229, compound

HRID 2165828Notes

Reaction equation

HRID 2165828 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][CH:14]([CH3:17])[CH2:15][OH:16].O.ClCCl>C(O)CCC>[Cl:12][C:8]1[CH:7]=[C:6]2[C:11]([C:2]([NH:13][CH:14]([CH3:17])[CH2:15][OH:16])=[CH:3][CH:4]=[N:5]2)=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 962WaterHCID 51262-AminopropanolHCID 6344DichloromethaneHCID 68664,7-Dichloroquinoline

Product 1

HCID 14209229HCID 14209229, compoundYield 71.1%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A mixture of 20 g of 4,7-dichloroquinoline and 16 g of 2-amino-1-propanol in 60 ml of butanol was stirred at reflux. The reaction was complete after three days of stirring and the vessel was allowed to cool to room temperature. Water was added to the mixture and extraction was conducted with dichloromethane. Drying over anhydrous magnesium sulfate and evaporation of solvents resulted in 17 g of solid which was triturated with ether. Recrystallization from ethanol/acetone gave 16 g of crystalline solid with a melting point of 210°-212° C.

Workup

  1. temperatureat reflux
  2. stirringof stirring
  3. dry with materialDrying over anhydrous magnesium sulfate and evaporation of solvents

Sources & evidence

ORD record
ord-efab6c887701431791739ad08cd8d732
Source dataset
uspto-grants-1990_07
Patent number
US04942168

Reaction notes

Loading…