Water → 3-[(Dipropylamino)carbonyl]-5-(8-quinolinyl)benzoic acid
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
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 6 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
- customthe reaction mixture is partitioned between ethyl acetate (10 mL) and water (10 mL)
- customThe aqueous phase is separated
- extractionextracted with chloroform (3×40 mL)
- washThe organic phase is washed with saline
- dry with materialdried (sodium sulfate)
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-9e18f2e31f8540688e4bf8128aefc95f
- Source dataset
- uspto-grants-2007_05
- Patent number
- US07214715B2
Reaction notes
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