Lithium Hydroxide → HCID 68290617, compound

HRID 2174566Notes

Reaction equation

HRID 2174566 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([OH:18])=[C:7]([C:13]([O:15]CC)=[O:14])[C:8](=[O:12])[NH:9]2)=[CH:4][C:3]=1[C:19]1[CH:24]=[CH:23][C:22]([C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([O:31][CH3:32])[C:26]=2[OH:33])=[CH:21][CH:20]=1.[OH-].[Li+]>C1COCC1.O>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([OH:18])=[C:7]([C:13]([OH:15])=[O:14])[C:8](=[O:12])[NH:9]2)=[CH:4][C:3]=1[C:19]1[CH:20]=[CH:21][C:22]([C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([O:31][CH3:32])[C:26]=2[OH:33])=[CH:23][CH:24]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 60198620HCID 60198620, compound

Product 1

HCID 68290617HCID 68290617, compoundYield 17.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To a suspension of ethyl 7-chloro-4-hydroxy-6-[2′-hydroxy-3′-(methyloxy)-4-biphenylyl]-2-oxo-1,2-dihydro-3-quinolinecarboxylate (Example 28) (150 mg, 0.322 mmol) in THF (4 mL) and water (2 mL) was added lithium hydroxide (100 mg, 2.4 mmol). The reaction mixture was stirred 48 h at 50° C. and 24 h at room temperature before being cooled down. The mixture was then evaporated, acidified with 1N HCl, filtered and dried. The resulting solid was triturated in hot acetonitrile, filtered and dried to give the title compound 7-chloro-4-hydroxy-6-[2′-hydroxy-3′-(methyloxy)-4-biphenylyl]-2-oxo-1,2-dihydro-3-quinolinecarboxylic acid (25 mg, 0.057 mmol, 17.7% yield) as cream solid. LCMS: (M−H)+=436; Rt=2.89 min. HRMS: calculated for C23H15ClNO6 (M−H)+: 436.0588. found: 436.0560.

Workup

  1. temperaturebefore being cooled down
  2. customThe mixture was then evaporated
  3. filtrationfiltered
  4. customdried
  5. customThe resulting solid was triturated in hot acetonitrile
  6. filtrationfiltered
  7. customdried

Sources & evidence

ORD record
ord-0b9f0e7b9e07423eaf89df907efacc85
Source dataset
uspto-grants-2015_06
Patent number
US09061998B2

Reaction notes

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