Potassium Hydroxide → HCID 22922143, compound

HRID 2258513Notes

Reaction equation

HRID 2258513 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([C:12]3[O:13][C:14]4[CH:20]=[C:19]([O:21][CH2:22][CH2:23][CH2:24][C:25]([O:27]CC)=[O:26])[CH:18]=[CH:17][C:15]=4[CH:16]=3)=[N:9]2)=[CH:4][CH:3]=1.[OH-].[K+]>C(O)C.O>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([C:12]3[O:13][C:14]4[CH:20]=[C:19]([O:21][CH2:22][CH2:23][CH2:24][C:25]([OH:27])=[O:26])[CH:18]=[CH:17][C:15]=4[CH:16]=3)=[N:9]2)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 22922137HCID 22922137, compound

Product 1

HCID 22922143HCID 22922143, compoundYield 55.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A mixture of 7-chloro-2-[6-[3-(ethoxycarbonyl)-propoxy]benzofuran-2-yl]quinoline (1.26 g) and potassium hydroxide (1.51 g) in a mixture of ethanol (12 ml) and water (6 ml) was stirred under reflux for one hour. After being cooled, the resulting precipitates were collected by filtration, washed with ethanol and added to water. The mixture was adjusted to pH 7 with diluted aqueous hydrochloric acid. The resulting crystals were collected by filtration, washed with water, and recrystallized from a mixture of acetic acid and methanol to give 7-chloro-2-[6-(3-carboxypropoxy)benzofuran-2-yl]quinoline (0.65 g).

Workup

  1. temperatureunder reflux for one hour
  2. temperatureAfter being cooled
  3. customthe resulting precipitates
  4. filtrationwere collected by filtration
  5. washwashed with ethanol
  6. additionadded to water
  7. filtrationThe resulting crystals were collected by filtration
  8. washwashed with water
  9. customrecrystallized from a mixture of acetic acid and methanol

Sources & evidence

ORD record
ord-8d0b28f522be4cf3a79d4afd6fa666db
Source dataset
uspto-grants-1997_08
Patent number
US05661159

Reaction notes

Loading…