Hydrochloric Acid → HCID 67171426, compound

HRID 551112Notes

Reaction equation

HRID 551112 reaction equation
C([O:3][C:4](=[O:36])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([CH:12]([C:24]2[C:33]([OH:34])=[C:32]3[C:27]([CH:28]=[CH:29][CH:30]=[N:31]3)=[C:26]([Cl:35])[CH:25]=2)[NH:13][C:14](=[O:23])[CH2:15][O:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:7]=1)C.[OH-].[Na+].Cl>C1COCC1>[Cl:35][C:26]1[CH:25]=[C:24]([CH:12]([NH:13][C:14](=[O:23])[CH2:15][O:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:8]2[CH:7]=[C:6]([CH2:5][C:4]([OH:36])=[O:3])[CH:11]=[CH:10][CH:9]=2)[C:33]([OH:34])=[C:32]2[C:27]=1[CH:28]=[CH:29][CH:30]=[N:31]2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 131728893HCID 131728893, compound

Product 1

HCID 67171426HCID 67171426, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The solution of 100 mg of ethyl(3-{(5-chloro-8-hydroxyquinolin-7-yl) [(phenoxyacetyl)amino]methyl}phenyl)acetate in THF and Sodium hydroxide (aqueous, 5 eq.) were stirred at room temperature for 48 h. The reaction mixture was acidified to pH 3 with 2N aq. HCl, then concentrated. The residue was diluted with methylene chloride, washed with water, dried over sodium sulfate and concentrated. Solids were triturated with ether and filtered to give 40 mg (43%) of (3-{(5-chloro-8-hydroxyquinolin-7-yl)[(phenoxyacetyl)amino]methyl}phenyl)acetic acid as a white solid.

Workup

  1. concentrationconcentrated
  2. additionThe residue was diluted with methylene chloride
  3. washwashed with water
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customSolids were triturated with ether
  7. filtrationfiltered

Sources & evidence

ORD record
ord-e140c875a8144454a7481dcdc62ec5fe
Source dataset
uspto-grants-2011_05
Patent number
US07947712B2

Reaction notes

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