Hydrochloric Acid → 6-{4-Chloro-3-[3-(dimethylamino)propoxy]phenyl}-5-(2,6-dimethoxyphenyl)pyridine-2-carboxylic acid

HRID 1639891Notes

Reaction equation

HRID 1639891 reaction equation
[OH-].[K+].[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:15]=[C:14]([C:16]([O:18]CC)=[O:17])[CH:13]=[CH:12][C:11]=2[C:21]2[C:26]([O:27][CH3:28])=[CH:25][CH:24]=[CH:23][C:22]=2[O:29][CH3:30])=[CH:6][C:5]=1[O:31][CH2:32][CH2:33][CH2:34][N:35]([CH3:37])[CH3:36].Cl>CCO>[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:15]=[C:14]([C:16]([OH:18])=[O:17])[CH:13]=[CH:12][C:11]=2[C:21]2[C:26]([O:27][CH3:28])=[CH:25][CH:24]=[CH:23][C:22]=2[O:29][CH3:30])=[CH:6][C:5]=1[O:31][CH2:32][CH2:33][CH2:34][N:35]([CH3:37])[CH3:36]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 66720729Ethyl 6-{4-chloro-3-[3-(dimethylamino)propoxy]phenyl)-5-(2,6-dimethoxyphenyl)pyridine-2-carboxylate

Product 1

HCID 667208756-{4-Chloro-3-[3-(dimethylamino)propoxy]phenyl}-5-(2,6-dimethoxyphenyl)pyridine-2-carboxylic acidYield 100%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Add 3.16 g (56.38 mmol) of potassium hydroxide to a solution of 5.63 g (11.28 mmol) of ethyl 6-{4-chloro-3-[3-(dimethylamino)propoxy]phenyl}-5-(2,6-dimethoxyphenyl)pyridine-2-carboxylate in 132 mL of EtOH. Reflux the reaction mixture for 2 h and then concentrate under reduced pressure. Take up the residue obtained in 10 mL of water, then neutralize with 56.5 mL (56.5 mmol) of a 1N HCl aqueous solution. The precipitate obtained is filtered on a frit and rinsed with 2×10 mL of water. After drying under reduced pressure, we obtain 5.25 g of 6-{4-chloro-3-[3-(dimethylamino)propoxy]phenyl}-5-(2,6-dimethoxyphenyl)pyridine-2-carboxylic acid in the form of white powder.

Workup

  1. temperatureReflux the reaction mixture for 2 h
  2. concentrationconcentrate under reduced pressure
  3. customobtained in 10 mL of water
  4. customThe precipitate obtained
  5. filtrationis filtered on a frit
  6. washrinsed with 2×10 mL of water
  7. customAfter drying under reduced pressure, we

Sources & evidence

ORD record
ord-5a28bf092d6b4926909ee4fa74384893
Source dataset
uspto-grants-2012_02
Patent number
US08110579B2

Reaction notes

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