Lithium Hydroxide → 3-(4-Carboxybenzyl)-7-chloro-4-oxo-1-phenyl-1,4-dihydroquinoline-2-carboxylic acid methyl ester

HRID 1697071Notes

Reaction equation

HRID 1697071 reaction equation
[CH3:1][O:2][C:3]([C:5]1[N:6]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:7]2[C:12]([C:13](=[O:26])[C:14]=1[CH2:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]([O:24]C)=[O:23])=[CH:18][CH:17]=1)=[CH:11][CH:10]=[C:9]([Cl:27])[CH:8]=2)=[O:4].[Li+].[OH-]>CO>[CH3:1][O:2][C:3]([C:5]1[N:6]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:7]2[C:12]([C:13](=[O:26])[C:14]=1[CH2:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]([OH:24])=[O:23])=[CH:18][CH:17]=1)=[CH:11][CH:10]=[C:9]([Cl:27])[CH:8]=2)=[O:4]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 598461727-Chloro-3-(4-methoxycarbonyl-benzyl)-4-oxo-1-phenyl-1,4-dihydro-quinoline-2-carboxylic acid methyl ester2×

Product 1

HCID 251817183-(4-Carboxybenzyl)-7-chloro-4-oxo-1-phenyl-1,4-dihydroquinoline-2-carboxylic acid methyl esterYield 36.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 7-chloro-3-(4-methoxycarbonyl-benzyl)-4-oxo-1-phenyl-1,4-dihydro-quinoline-2-carboxylic acid methyl ester (compound 10, 31 mg) and LiOH (1 M aq, 1 mL) in MeOH (10 mL) was stirred at RT overnight. The reaction mixture was then stirred at 50° C. for 3 h, then extracted with EtOAc. The organic layer was separated, the aqueous layer acidified by adding AcOH (aq), and the resulting mixture extracted with EtOAc. The combined organic extracts were dried over Na2SO4, filtered and evaporated under reduced pressure. The crude residue was purified by preparative TLC (hexane/acetone, 70:30+1% AcOH) to afford 11 mg of 3-(4-carboxybenzyl)-7-chloro-4-oxo-1-phenyl-1,4-dihydroquinoline-2-carboxylic acid methyl ester as an off-white solid. MS=447; MP=258.0-261.0° C.

Workup

  1. stirringThe reaction mixture was then stirred at 50° C. for 3 h
  2. extractionextracted with EtOAc
  3. customThe organic layer was separated
  4. additionby adding AcOH (aq)
  5. extractionthe resulting mixture extracted with EtOAc
  6. dry with materialThe combined organic extracts were dried over Na2SO4
  7. filtrationfiltered
  8. customevaporated under reduced pressure
  9. customThe crude residue was purified by preparative TLC (hexane/acetone, 70:30+1% AcOH)

Sources & evidence

ORD record
ord-f98418cdb82d4660a4e56e07d02f8b9f
Source dataset
uspto-grants-2012_04
Patent number
US08163906B2

Reaction notes

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