Sodium Hydroxide → 1-(4-Fluoro-benzyl)-2-oxo-1,2-dihydro-pyridine-3-carboxylic acid

HRID 347543ノート

反応式

HRID 347543 の反応式
[F:1][C:2]1[CH:19]=[CH:18][C:5]([CH2:6][N:7]2[CH:12]=[CH:11][CH:10]=[C:9]([C:13]([O:15]C)=[O:14])[C:8]2=[O:17])=[CH:4][CH:3]=1.[OH-].[Na+]>CO>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[CH:12]=[CH:11][CH:10]=[C:9]([C:13]([OH:15])=[O:14])[C:8]2=[O:17])=[CH:18][CH:19]=1

参加物

4

反応物 2

HCID 14798Sodium HydroxideHCID 21081722Methyl 1-(4-fluorobenzyl)-2-oxo-1,2-dihydropyridine-3-carboxylate

生成物 1

HCID 168966831-(4-Fluoro-benzyl)-2-oxo-1,2-dihydro-pyridine-3-carboxylic acid収率 70.3%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
0 °C

実験手順

A solution of methyl 1-(4-fluorobenzyl)-2-oxo-1,2-dihydropyridine-3-carboxylate (2.4 g, 9.2 mmol, 1.0 eq) in MeOH (25 ml) was treated with 5 N aqueous sodium hydroxide (4.6 mL, 24 mmol, 2.6 eq) at room temperature and the reaction mixture was stirred for 15 h. The reaction mixture was concentrated in vacuo, diluted with water and the solution was extracted with ethyl acetate (discarding the organic fraction). The aqueous fraction was cooled to 0° C. and acidified with concentrated HCl. The resulting solid was filtered, washed with water and the solid dried in vacuo to afford the product (1.6 g, 70%) which was sufficiently pure to use in the subsequent step without further purification. 1H NMR (DMSO-d6) δ 8.44–8.39 (m, 2H), 7.46–7.42 (m, 2H), 7.24–7.18 (m, 2H), 6.78 (d, 1H, J=6.98 Hz), 5.31 (s, 2H); HRMS(ESI), calcd.: 248.0723, found: 248.0718.

後処理

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. additiondiluted with water
  3. extractionthe solution was extracted with ethyl acetate (
  4. filtrationThe resulting solid was filtered
  5. washwashed with water
  6. customthe solid dried in vacuo

出典と根拠

ORDレコード
ord-f0bf1cb336424f24ac8e4e0fa99e5073
出典データセット
uspto-grants-2007_02
特許番号
US07173031B2

反応ノート

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