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

HRID 2403670노트

반응식

HRID 2403670 반응식
[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]

참가 물질

6

반응물 2

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

생성물 1

HCID 180713662-Carbamoyl-1H-indole-5-carboxylic acid수율 82%

시약·촉매·용매 3

HCID 174Ethylene Glycol용매HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-3504e90373084e05af1f489294348b0a
출처 데이터셋
uspto-grants-2014_08
특허 번호
US08802688B2

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