Hydrochloric Acid → HCID 66841260, compound

HRID 244062Notes

Reaction equation

HRID 244062 reaction equation
[Cl:1][C:2]1[C:3]([C:9]2[C:10]([C:18]3[CH:23]=[CH:22][C:21]([Cl:24])=[C:20]([O:25][CH2:26][CH2:27][CH2:28][N:29]([CH3:31])[CH3:30])[CH:19]=3)=[N:11][C:12]([C:15]([O-:17])=[O:16])=[CH:13][CH:14]=2)=[N:4][CH:5]=[C:6]([Cl:8])[CH:7]=1.[OH-].[K+].Cl.C(Cl)Cl.CO>CCO.O>[Cl:1][C:2]1[C:3]([C:9]2[C:10]([C:18]3[CH:23]=[CH:22][C:21]([Cl:24])=[C:20]([O:25][CH2:26][CH2:27][CH2:28][N:29]([CH3:30])[CH3:31])[CH:19]=3)=[N:11][C:12]([C:15]([OH:17])=[O:16])=[CH:13][CH:14]=2)=[N:4][CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 21226129Dichloromethane methanolHCID 86649788HCID 86649788, compound

Product 1

HCID 66841260HCID 66841260, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of 1.82 g (3.9 mmol) of 3,5-dichloro-2′-{4-chloro-3-[3-(dimethylamino)propoxy]phenyl}-2,3′-bipyridine-6′-carboxylate in 50 mL of EtOH and 10 ml of water is added 0.34 g (6.06 mmol) of KOH. The reaction medium is stirred for 18 hours at room temperature, and then concentrated under reduced pressure. The residue obtained is taken up in 6.1 mL of aqueous 1N HCl solution (6.1 mmol) and 100 ml of a 9/1 DCM/MeOH mixture. The organic phase is dried over Na2SO4 and then concentrated under reduced pressure, to give 1.8 g of 3,5-dichloro-2′-{4-chloro-3-[3-(dimethylamino)propoxy]phenyl}-2,3′-bipyridine-6′-carboxylic acid in the form of a gum.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe residue obtained
  3. dry with materialThe organic phase is dried over Na2SO4
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-9bcdf898927d49e8b1731c230c450968
Source dataset
uspto-grants-2014_02
Patent number
US08653276B2

Reaction notes

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