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

HRID 1672951노트

반응식

HRID 1672951 반응식
[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

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 19096565Water ethanol용매

반응 조건

온도
60 °C

실험 절차

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−).

후처리

  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

출처 및 근거

ORD 기록
ord-84beb474cc0741b985fb04a83b9d8975
출처 데이터셋
uspto-grants-2011_08
특허 번호
US07999006B2

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