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Methanol → 4-[[2-(4-Hydroxy-1-Piperidyl)Quinoline-4-carbonyl]amino]-3,5-dimethyl-benzoic acid

HRID 1427132
Notes
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Reaction equation

HRID 1427132 reaction equation
[OH-].[Na+].[OH:3][CH:4]1[CH2:9][CH2:8][N:7]([C:10]2[CH:19]=[C:18]([C:20]([NH:22][C:23]3[C:32]([CH3:33])=[CH:31][C:26]([C:27]([O:29]C)=[O:28])=[CH:25][C:24]=3[CH3:34])=[O:21])[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[N:11]=2)[CH2:6][CH2:5]1.CO>C1COCC1>[OH:3][CH:4]1[CH2:5][CH2:6][N:7]([C:10]2[CH:19]=[C:18]([C:20]([NH:22][C:23]3[C:24]([CH3:34])=[CH:25][C:26]([C:27]([OH:29])=[O:28])=[CH:31][C:32]=3[CH3:33])=[O:21])[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[N:11]=2)[CH2:8][CH2:9]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 86707365Methyl 4-[[2-(4-Hydroxy-1-Piperidyl)Quinoline-4-carbonyl]Amino]-3,5-dimethyl-benzoate

Product 1

HCID 867073664-[[2-(4-Hydroxy-1-Piperidyl)Quinoline-4-carbonyl]amino]-3,5-dimethyl-benzoic acidYield 40%

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent

Procedure

A solution of aqueous 2N NaOH (2.00 ml) is added to a stirred solution of methyl 4-(2-(4-hydroxypiperidin-1-yl)quinoline-4-carboxamido)-3,5-dimethylbenzoate (0.13 g, 0.0003 mol) in THF:MeOH (5 ml:2 ml). After 5 h at 50° C., the organic solvent is removed under reduced pressure and the residue is diluted with water acidified to pH 6 with aqueous 1N HCl and extracted with ethyl acetate (2×20 ml). The organic layers are combined and dried over anhydrous sodium sulfate. The solvent is removed under reduced pressure and the resulting precipitate is triturated with pentane and diethyl ether and filtered to afford the title compound as a light yellow solid (0.05 g, 40%). Mass spectrum (m/z): 420.2 (M+1).

Workup

  1. customthe organic solvent is removed under reduced pressure
  2. additionthe residue is diluted with water
  3. extractionextracted with ethyl acetate (2×20 ml)
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent is removed under reduced pressure
  6. customthe resulting precipitate is triturated with pentane and diethyl ether
  7. filtrationfiltered

Sources & evidence

ORD record
ord-88868ade68654d55a3673ca60de13aaf
Source dataset
uspto-grants-2015_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08933098B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes