Water → HCID 22915630, compound

HRID 1377970Notes

Reaction equation

HRID 1377970 reaction equation
[CH2:1]([C:5]1[N:6]([CH2:13][C:14]2[CH:15]=[C:16]3[C:21](=[CH:22][CH:23]=2)[N:20]=[C:19]([C:24]2[CH:33]=[CH:32][CH:31]=[CH:30][C:25]=2[C:26]([O:28]C)=[O:27])[CH:18]=[CH:17]3)[C:7]([CH:11]=[O:12])=[C:8]([Cl:10])[N:9]=1)[CH2:2][CH2:3][CH3:4].[OH-].[Na+].O>C(O)C>[CH2:1]([C:5]1[N:6]([CH2:13][C:14]2[CH:15]=[C:16]3[C:21](=[CH:22][CH:23]=2)[N:20]=[C:19]([C:24]2[CH:33]=[CH:32][CH:31]=[CH:30][C:25]=2[C:26]([OH:28])=[O:27])[CH:18]=[CH:17]3)[C:7]([CH:11]=[O:12])=[C:8]([Cl:10])[N:9]=1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 15816899HCID 15816899, compound

Product 1

HCID 22915630HCID 22915630, compoundYield 78.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

186 mg (0.403 mmol) of methyl 2-{6-[(2-butyl-4-chloro-5-formyl-1H-imidazol-1-yl)methyl]quinolin-2-yl}benzoate obtained in Example 1 was mixed with 19.3 mg (0.484 mmol) of sodium hydroxide, 1 ml of water and 2 ml of ethanol and the mixture was stirred at room temperature for 24 hours. Then, the mixture was concentrated under reduced pressure and the concentrate was partitioned between water and ether. The aqueous layer was acidified with 1N hydrochloric acid and extracted with ethyl acetate. The organic layer was dried over magnesium sulfate followed by filtration. The resulting filtrate was concentrated under reduced pressure to obtain 142 mg of 2-{6-[(2-butyl-4-chloro-5-formyl-1H-imidazol-1-yl)methyl]quinolin-2-yl}benzoic acid.

Workup

  1. concentrationThen, the mixture was concentrated under reduced pressure
  2. customthe concentrate was partitioned between water and ether
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. filtrationfollowed by filtration
  6. concentrationThe resulting filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-c582c5fc6c184a0e9543e118b3ec8c00
Source dataset
uspto-grants-1997_09
Patent number
US05665881

Reaction notes

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