Hydrochloric Acid → 8-[3-[N-(3-carboxypropionyl)-N-methylamino]-2,6-dichlorobenzyloxy]-2-methylquinoline

HRID 1604600Notes

Reaction equation

HRID 1604600 reaction equation
[Cl:1][C:2]1[C:20]([N:21]([C:23](=[O:30])[CH2:24][CH2:25][C:26]([O:28]C)=[O:27])[CH3:22])=[CH:19][CH:18]=[C:17]([Cl:31])[C:3]=1[CH2:4][O:5][C:6]1[CH:7]=[CH:8][CH:9]=[C:10]2[C:15]=1[N:14]=[C:13]([CH3:16])[CH:12]=[CH:11]2.[OH-].[Na+].Cl>CO.C(Cl)(Cl)Cl>[C:26]([CH2:25][CH2:24][C:23]([N:21]([C:20]1[C:2]([Cl:1])=[C:3]([C:17]([Cl:31])=[CH:18][CH:19]=1)[CH2:4][O:5][C:6]1[CH:7]=[CH:8][CH:9]=[C:10]2[C:15]=1[N:14]=[C:13]([CH3:16])[CH:12]=[CH:11]2)[CH3:22])=[O:30])([OH:28])=[O:27]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 19603281HCID 19603281, compound

Product 1

HCID 196033388-[3-[N-(3-carboxypropionyl)-N-methylamino]-2,6-dichlorobenzyloxy]-2-methylquinolineYield 82.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6212ChloroformSolvent

Procedure

To a solution of 8-[2,6-dichloro-3-[N-(3-methoxycarbonylpropionyl)-N-methylamino]benzyloxy]-2-methylquinoline (303 mg) in methanol (3 ml) was added 1N aqueous solution of sodium hydroxide (1.0 ml) at ambient temperature. The mixture was stirred for 1 hour and neutralized to pH 4 with 1N hydrochloric acid. The reaction mixture was diluted with chloroform and washed with water. The aqueous layer was saturated with sodium chloride and extracted with chloroform. The combined organic layers were dried over magnesium sulfate and evaporated in vacuo to give 8-[3-[N-(3-carboxypropionyl)-N-methylamino]-2,6-dichlorobenzyloxy]-2-methylquinoline (242 mg) as an off-white powder.

Workup

  1. washwashed with water
  2. extractionextracted with chloroform
  3. dry with materialThe combined organic layers were dried over magnesium sulfate
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-f12b1744cb1c42daac78f1c6da3deb0c
Source dataset
uspto-grants-1999_11
Patent number
US05994368

Reaction notes

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