Water → 4-(2-chloroethyl)-6-methoxy-2(1H)-quinolone

HRID 619112Notes

Reaction equation

HRID 619112 reaction equation
S(Cl)([Cl:3])=O.O[CH2:6][CH2:7][C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([O:18][CH3:19])[CH:16]=2)[NH:11][C:10](=[O:20])[CH:9]=1.O>C(Cl)(Cl)Cl.CN(C)C=O>[Cl:3][CH2:6][CH2:7][C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([O:18][CH3:19])[CH:16]=2)[NH:11][C:10](=[O:20])[CH:9]=1

Participants

6

Reactant 3

HCID 962WaterHCID 24386Thionyl ChlorideHCID 218460254-(2-hydroxyethyl)-6-methoxy-2(1H)-quinolone

Product 1

HCID 153886994-(2-chloroethyl)-6-methoxy-2(1H)-quinoloneYield 94.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6212ChloroformSolvent

Procedure

3.4 ml (46.6 mmol) of thionyl chloride are added while stirring at room temperature to a suspension of 3.11 g (14.2 mmol) of 4-(2-hydroxyethyl)-6-methoxy-2(1H)-quinolone in 50 ml of chloroform and 3 drops of dimethylformamide. The suspension is heated to reflux for 14 hours (total solubilization). After cooling to room temperature, 50 ml of water are added dropwise to the reaction medium and the mixture is left stirring for 30 minutes. The organic phase is recovered, separated after settling has taken place, washed with water, dried over magnesium sulphate and filtered. The filtrate is concentrated under vacuum. 3.2 g of a pale yellow solid are obtained.

Workup

  1. temperatureThe suspension is heated
  2. temperatureto reflux for 14 hours (total solubilization)
  3. waitthe mixture is left
  4. customThe organic phase is recovered
  5. customseparated after settling
  6. washwashed with water
  7. dry with materialdried over magnesium sulphate
  8. filtrationfiltered
  9. concentrationThe filtrate is concentrated under vacuum

Sources & evidence

ORD record
ord-599b4728d02a4e8e9058a51457ac7392
Source dataset
uspto-grants-1999_09
Patent number
US05958924

Reaction notes

Loading…