Water → 3-[(Dipropylamino)carbonyl]-5-(8-quinolinyl)benzoic acid

HRID 14031Notes

Reaction equation

HRID 14031 reaction equation
[CH2:1]([N:4]([CH2:27][CH2:28][CH3:29])[C:5]([C:7]1[CH:8]=[C:9]([CH:14]=[C:15]([C:17]2[CH:18]=[CH:19][CH:20]=[C:21]3[C:26]=2[N:25]=[CH:24][CH:23]=[CH:22]3)[CH:16]=1)[C:10]([O:12]C)=[O:11])=[O:6])[CH2:2][CH3:3].[OH-].[Li+].O>CO>[CH2:27]([N:4]([CH2:1][CH2:2][CH3:3])[C:5]([C:7]1[CH:8]=[C:9]([CH:14]=[C:15]([C:17]2[CH:18]=[CH:19][CH:20]=[C:21]3[C:26]=2[N:25]=[CH:24][CH:23]=[CH:22]3)[CH:16]=1)[C:10]([OH:12])=[O:11])=[O:6])[CH2:28][CH3:29]

Participants

5

Reactant 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 21086177Methyl 3-[(dipropylamino)carbonyl]-5-(8-quinolinyl)benzoate

Product 1

HCID 210857893-[(Dipropylamino)carbonyl]-5-(8-quinolinyl)benzoic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a mixture of methyl 3-[(dipropylamino)carbonyl]-5-(8-quinolinyl)benzoate (XLIX, step 1, 175.5 mg, 0-45 mmol) in methanol (2 mL) is added lithium hydroxide (32.3 mg, 1.4 mmol) and water (500 microliter). After stirring overnight, the reaction mixture is partitioned between ethyl acetate (10 mL) and water (10 mL). The aqueous phase is separated and acidified with hydrochloric acid (1N), and extracted with chloroform (3×40 mL). The organic phase is washed with saline, dried (sodium sulfate) and concentrated under reduced pressure to give 3-[(dipropylamino)carbonyl]-5-(8-quinolinyl)benzoic acid (IX-L, 130 mg), NMR (300 MHz, CD3OD) δ 8.84, 8.39, 8.35, 8.05, 7.96, 7.90, 7.87, 7.79, 7.68, 3.50, 3.37, 1.76-1.61, 0.99 and 0.84.

Workup

  1. customthe reaction mixture is partitioned between ethyl acetate (10 mL) and water (10 mL)
  2. customThe aqueous phase is separated
  3. extractionextracted with chloroform (3×40 mL)
  4. washThe organic phase is washed with saline
  5. dry with materialdried (sodium sulfate)
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-773fe46c2a8a46039e2bb4dbb050ab9d
Source dataset
uspto-grants-2010_06
Patent number
US07727997B2

Reaction notes

Loading…