Pyridine → 3-chloro-N-[5-chloro-2-hydroxy-4-trifluoromethylphenyl]isonicotinamide

HRID 884959

반응식

HRID 884959 반응식
[NH2:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([C:9]([F:12])([F:11])[F:10])=[CH:4][C:3]=1[OH:13].[Cl:14][C:15]1[CH:23]=[N:22][CH:21]=[CH:20][C:16]=1[C:17](O)=[O:18].CCN=C=NCCCN(C)C.N1C=CC=CC=1>O>[Cl:14][C:15]1[CH:23]=[N:22][CH:21]=[CH:20][C:16]=1[C:17]([NH:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([C:9]([F:12])([F:10])[F:11])=[CH:4][C:3]=1[OH:13])=[O:18]

참가 물질

6

반응물 4

HCID 1049PyridineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 27358163-Chloropyridine-4-carboxylic acidHCID 668804782-Amino-4-chloro-5-(trifluoromethyl)phenol

생성물 1

HCID 668807913-chloro-N-[5-chloro-2-hydroxy-4-trifluoromethylphenyl]isonicotinamide수율 69.9%

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
80 °C

실험 절차

A mixture of 0.60 g of 2-amino-4-chloro-5-trifluoromethylphenol, 0.43 g of 3-chloroisonicotinic acid, 0.67 g of WSC and 5 ml of pyridine was stirred while heating at 80° C. for three hours. The reaction mixture was cooled to room temperature, and then water was added, followed by extraction with ethyl acetate three times. The combined organic layers were washed with water and a saturated sodium chloride solution, dried anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 0.67 g of 3-chloro-N-[5-chloro-2-hydroxy-4-trifluoromethylphenyl]isonicotinamide.

후처리

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionfollowed by extraction with ethyl acetate three times
  3. washThe combined organic layers were washed with water
  4. concentrationa saturated sodium chloride solution, dried anhydrous magnesium sulfate, and then concentrated under reduced pressure

출처 및 근거

ORD 기록
ord-729614d889394d2598aae2e6066655e1
출처 데이터셋
uspto-grants-2012_08
특허 번호
US08242133B2

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