Sodium Hydroxide → 4-(2-Fluoro-4-iodoanilino)-1-methyl-6-oxo-1,6-dihydro-3-pyridinecarboxylic acid

HRID 917695ノート

反応式

HRID 917695 の反応式
C([O:3][C:4]([C:6]1[C:11]([NH:12][C:13]2[CH:18]=[CH:17][C:16]([I:19])=[CH:15][C:14]=2[F:20])=[CH:10][C:9](=[O:21])[N:8]([CH3:22])[CH:7]=1)=[O:5])C.[OH-].[Na+]>CCO>[F:20][C:14]1[CH:15]=[C:16]([I:19])[CH:17]=[CH:18][C:13]=1[NH:12][C:11]1[C:6]([C:4]([OH:5])=[O:3])=[CH:7][N:8]([CH3:22])[C:9](=[O:21])[CH:10]=1

参加物

4

反応物 2

HCID 14798Sodium HydroxideHCID 11362025Ethyl 4-(2-fluoro-4-iodoanilino)-1-methyl-6-oxo-1,6-dihydro-3-pyridinecarboxylate

生成物 1

HCID 112346084-(2-Fluoro-4-iodoanilino)-1-methyl-6-oxo-1,6-dihydro-3-pyridinecarboxylic acid収率 96%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
70 °C

実験手順

4-(2-Fluoro-4-iodo-phenylamino)-1-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid ethyl ester was dissolved in EtOH (100 mL) and treated with NaOH (2.60 g, 72.0 mmol). This mixture was stirred at 70° C. for 20 hours. The mixture was cooled to room temperature and solvent was removed under reduced pressure. The residue was acidified with 1N HCl then the resulting precipitate was filtered and washed with water. The solid was dried under high vacuum pump to afford 4-(2-Fluoro-4-iodo-phenylamino)-1-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid as a white solid (9.0 g, 96%). 1H NMR [(CD3)2SO, 400 MHz] δ 13.27(v br s, 1H), 9.60 (s, 1H), 8.49 (s, 1H), 7.74 (dd, J=10.1, 1.9 Hz, 1H), 7.59 (dd, J=8.4, 1.7, 0.8 Hz, 1H), 7.29 (dd, J=8.5 Hz, 1H), 5.48 (dd, J=0.7 Hz, 1H), 3.38 (s, 3H). (APCI+) calcd for C13H10FIN2O3 388.13 (M−1), found 386.9.

後処理

  1. temperatureThe mixture was cooled to room temperature
  2. customsolvent was removed under reduced pressure
  3. filtrationthe resulting precipitate was filtered
  4. washwashed with water
  5. customThe solid was dried under high vacuum pump

出典と根拠

ORDレコード
ord-e52361a7af4d4b45b64b82ad3edf6d8b
出典データセット
uspto-grants-2007_09
特許番号
US07273877B2

反応ノート

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