Methanol → 3-[[2-(4-Hydroxy-1-piperidyl)quinoline-4-carbonyl]amino]-2,4-dimethyl-benzoic acid

HRID 1427136ノート

反応式

HRID 1427136 の反応式
[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:24]([CH3:34])=[C:25]([CH:30]=[CH:31][C:32]=3[CH3:33])[C:26]([O:28]C)=[O:27])=[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[CH2:9][CH2:8][N:7]([C:10]2[CH:19]=[C:18]([C:20]([NH:22][C:23]3[C:24]([CH3:34])=[C:25]([CH:30]=[CH:31][C:32]=3[CH3:33])[C:26]([OH:28])=[O:27])=[O:21])[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[N:11]=2)[CH2:6][CH2:5]1

参加物

5

反応物 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 86707369Methyl 3-[[2-(4-hydroxy-1-piperidyl)quinoline-4-carbonyl]amino]-2,4-dimethyl-benzoate

生成物 1

HCID 867073703-[[2-(4-Hydroxy-1-piperidyl)quinoline-4-carbonyl]amino]-2,4-dimethyl-benzoic acid収率 31.1%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of aqueous 2N NaOH (2.00 ml) is added to a stirred solution of methyl 3-(2-(4-hydroxypiperidin-1-yl)quinoline-4-carboxamido)-2,4-dimethylbenzoate (0.10 g, 0.00023 mol) in THF:MeOH (4 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 (0.03 g, 31%). Mass spectrum (m/z): 420.2 (M+1).

後処理

  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

出典と根拠

ORDレコード
ord-d8de3b2434034cdfabe9bdad39ce190a
出典データセット
uspto-grants-2015_01
特許番号
US08933098B2

反応ノート

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