Hydrochloric Acid → 2-{1-[8-(2,4-Dichlorophenyl)-2-methylquinolin-4-yl]-piperidin-4-ylidene}acetic acid

HRID 23551Notes

Reaction equation

HRID 23551 reaction equation
[OH-:1].[K+].O.[Cl:4][C:5]1[CH:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:6]=1[C:12]1[CH:13]=[CH:14][CH:15]=[C:16]2[C:21]=1[N:20]=[C:19]([CH3:22])[CH:18]=[C:17]2[N:23]1[CH2:28][CH2:27][CH:26](C(OCC)=O)[CH2:25][C:24]1=C.Cl.[CH2:36]([OH:38])[CH3:37]>>[Cl:4][C:5]1[CH:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:6]=1[C:12]1[CH:13]=[CH:14][CH:15]=[C:16]2[C:21]=1[N:20]=[C:19]([CH3:22])[CH:18]=[C:17]2[N:23]1[CH2:28][CH2:27][C:26](=[CH:37][C:36]([OH:1])=[O:38])[CH2:25][CH2:24]1

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 702EthanolHCID 962WaterHCID 14797Potassium HydroxideHCID 225744318-(2,4-Dichlorophenyl)-2-methyl-4-(4-ethoxycarbonyl-methylidenepiperidin-1-yl)quinoline

Product 1

HCID 121346682-{1-[8-(2,4-Dichlorophenyl)-2-methylquinolin-4-yl]-piperidin-4-ylidene}acetic acid

Procedure

In a mixed solvent of 85% potassium hydroxide (1.3 g) and water (1.4 mL)-ethanol (8 mL), 8-(2,4-dichlorophenyl)-2-methyl-4-(4-ethoxycarbonyl-methylidenepiperidin-1-yl)quinoline (2.3 g) was stirred at 80° C. for 1 hour. The reaction mixture was neutralized with 3 M hydrochloric acid under ice-cooling and stirred under ice-cooling for 2 hours and then at room temperature for 30 minutes. The solid precipitated was collected by filtration to obtain a mixture (1.5 g) of 2-{1-[8-(2,4-dichlorophenyl)-2-methylquinolin-4-yl]-piperidin-4-ylidene}acetic acid and 2-{1-[8-(2,4-dichlorophenyl)-2-methylquinolin-4-yl]-1,2,3,6-tetrahydropyridin-4-yl}acetic acid.

Workup

  1. temperaturecooling
  2. temperaturecooling for 2 hours
  3. customThe solid precipitated
  4. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-c9ea102d16034504b8ea8da42f826b94
Source dataset
uspto-grants-2005_02
Patent number
US06852732B2

Reaction notes

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