Water → 5-Chloro-8-(2,2-diethoxyethoxy)quinoline

HRID 1650586Notes

Reaction equation

HRID 1650586 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:9]([OH:12])=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.[CH2:13]([O:15][CH:16]([O:19][CH2:20][CH3:21])[CH2:17]Br)[CH3:14].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[CH2:13]([O:15][CH:16]([O:19][CH2:20][CH3:21])[CH2:17][O:12][C:9]1[CH:10]=[CH:11][C:2]([Cl:1])=[C:3]2[C:8]=1[N:7]=[CH:6][CH:5]=[CH:4]2)[CH3:14]

Participants

6

Reactant 4

HCID 962WaterHCID 28175-Chloro-8-hydroxyquinolineHCID 11430Potassium CarbonateHCID 74852Ethane, 2-bromo-1,1-diethoxy-

Product 1

HCID 140311845-Chloro-8-(2,2-diethoxyethoxy)quinoline

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

180 g of 5-chloro-8-hydroxyquinoline, 237 g of 2-bromoacetaldehyde diethyl acetal and 200 g of potassium carbonate are stirred for 4 h at 120° C. in 800 ml of dimethylformamide. After cooling, the mixture is poured into 2.5 liters of water, and the product is filtered off under suction and dried in vacuo, melting point 51°-53° C.

Workup

  1. temperatureAfter cooling
  2. filtrationthe product is filtered off under suction
  3. customdried in vacuo, melting point 51°-53° C.

Sources & evidence

ORD record
ord-ee2e93792f0f4c309496a5b499e65c69
Source dataset
uspto-grants-1990_05
Patent number
US04925478

Reaction notes

Loading…