Potassium Hydroxide → 4-[(2-Fluoro-4-iodophenyl)amino]thiophene-3-carboxylic acid

HRID 605751ノート

反応式

HRID 605751 の反応式
[F:1][C:2]1[CH:7]=[C:6]([I:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10]1[C:11]([C:15]([O:17]C)=[O:16])=[CH:12][S:13][CH:14]=1.[OH-].[K+]>C(O)C.O.O>[F:1][C:2]1[CH:7]=[C:6]([I:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10]1[C:11]([C:15]([OH:17])=[O:16])=[CH:12][S:13][CH:14]=1

参加物

5

反応物 2

HCID 14797Potassium HydroxideHCID 66617354Methyl 4-[(2-fluoro-4-iodophenyl)amino]thiophene-3-carboxylate

生成物 1

HCID 666174654-[(2-Fluoro-4-iodophenyl)amino]thiophene-3-carboxylic acid収率 83%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 19096565Water ethanol溶媒

反応条件

温度
60 °C

実験手順

A mixture of methyl 4-[(2-fluoro-4-iodophenyl)amino]thiophene-3-carboxylate (0.74 g, 1.96 mmol) in the solution of potassium hydroxide (0.3 g) in ethanol/water (4 ml/4 ml) was heated up to 60° C. and stirred at this temperature for 30 min. The mixture was cooled to room temperature, diluted with 4 ml of water and extracted with ether. The water layer was acidified with 1 N HCl to pH 2, the product precipitated and was filtered off, washed several times with water and dried in vacuo to afford 4-[(2-fluoro-4-iodophenyl)amino]thiophene-3-carboxylic acid (0.59 g, 83%). 1H NMR (d6-DMSO): 13.20 (s, 1H), 9.13 (s, 1H), 8.35 (d, 1H), 7.62 (dd, 1H), 7.48-7.38 (m, 2H), 7.11 (s, 1H); MS (EI) for C11H7FINO2S: 362 (MH−).

後処理

  1. temperatureThe mixture was cooled to room temperature
  2. extractionextracted with ether
  3. customthe product precipitated
  4. filtrationwas filtered off
  5. washwashed several times with water
  6. customdried in vacuo

出典と根拠

ORDレコード
ord-d5197262fc8548cb913a28007adb281d
出典データセット
uspto-grants-2011_03
特許番号
US07915250B2

反応ノート

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