Potassium Hydroxide → 2-Carbamoyl-1H-indole-5-carboxylic acid

HRID 2403670ノート

反応式

HRID 2403670 の反応式
[C:1]([C:4]1[NH:5][C:6]2[C:11]([CH:12]=1)=[CH:10][C:9]([C:13]([O:15]C)=[O:14])=[CH:8][CH:7]=2)(=[O:3])[NH2:2].[OH-].[K+]>O1CCCC1.C(O)CO.O>[C:1]([C:4]1[NH:5][C:6]2[C:11]([CH:12]=1)=[CH:10][C:9]([C:13]([OH:15])=[O:14])=[CH:8][CH:7]=2)(=[O:3])[NH2:2]

参加物

6

反応物 2

HCID 14797Potassium HydroxideHCID 70896052methyl 2-carbamoyl-1H-indole-5-carboxylate

生成物 1

HCID 180713662-Carbamoyl-1H-indole-5-carboxylic acid収率 82%

試薬・触媒・溶媒 3

HCID 174Ethylene Glycol溶媒HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a suspension of methyl 2-carbamoyl-1H-indole-5-carboxylate (300 mg, 1.38 mmol) in tetrahydrofuran (4.5 mL) and ethylene glycol (4.5 mL) was added potassium hydroxide (3.16 g, 56.4 mmol). The mixture was heated to reflux and stirred for 2 hours. The reaction was cooled to room temperature and diluted with water. The tetrahydrofuran was removed under reduced pressure. The solids were filtered off and the filtrate was acidified to pH 4 with concentrated hydrochloric acid. The resulting precipitate was collected by filtration and dried under vacuum to give 2-carbamoyl-1H-indole-5-carboxylic acid (230 mg, 82%). 1H NMR (400 MHz, DMSO-d6, δ): 12.53 (br. s., 1 H), 11.88 (br. s., 1 H), 8.28 (s, 1 H), 8.04 (br. s., 1 H), 7.77 (d, J=8.6 Hz, 1 H), 7.46 (m, J=8.6 Hz, 2 H), 7.25 (s, 1 H).

後処理

  1. temperatureThe mixture was heated
  2. temperatureto reflux
  3. customThe tetrahydrofuran was removed under reduced pressure
  4. filtrationThe solids were filtered off
  5. filtrationThe resulting precipitate was collected by filtration
  6. customdried under vacuum

出典と根拠

ORDレコード
ord-3504e90373084e05af1f489294348b0a
出典データセット
uspto-grants-2014_08
特許番号
US08802688B2

反応ノート

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