Pyridine → N-(4-chloropyridin-3-yl)-2-nitrobenzamide

HRID 44239

반응식

HRID 44239 반응식
[NH2:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[Cl:8].[N+:9]([C:12]1[CH:20]=[CH:19][CH:18]=[CH:17][C:13]=1[C:14](Cl)=[O:15])([O-:11])=[O:10].N1C=CC=CC=1>O1CCCC1>[Cl:8][C:7]1[CH:6]=[CH:5][N:4]=[CH:3][C:2]=1[NH:1][C:14](=[O:15])[C:13]1[CH:17]=[CH:18][CH:19]=[CH:20][C:12]=1[N+:9]([O-:11])=[O:10]

참가 물질

5

반응물 3

HCID 1049PyridineHCID 118752-Nitrobenzoyl chlorideHCID 5819323-Amino-4-chloropyridine

생성물 1

HCID 67434091N-(4-chloropyridin-3-yl)-2-nitrobenzamide

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A solution of 3-amino-4-chloropyridine (5 g, 39 mmol), 2-nitrobenzoyl chloride (5.1 mL, 39 mmol) and pyridine (11 mL) in tetrahydrofuran (50 mL) was stirred for 20 hours. The reaction mixture was partitioned between water (200 mL) and dichloromethane (600 mL). The phases were separated and the organic phase was washed with water (150 mL) then brine (150 mL). The organic phase was dried over sodium sulfate, filtered and concentrated in vacuo. The crude product was purified by flash chromatography (SiO2, 10% ethyl acetate in dichloromethane). The N-(4-chloropyridin-3-yl)-2-nitrobenzamide was obtained as a brown solid (2.0 g). LCMS [M+H]: 279.

후처리

  1. customThe reaction mixture was partitioned between water (200 mL) and dichloromethane (600 mL)
  2. customThe phases were separated
  3. washthe organic phase was washed with water (150 mL)
  4. dry with materialThe organic phase was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude product was purified by flash chromatography (SiO2, 10% ethyl acetate in dichloromethane)

출처 및 근거

ORD 기록
ord-fa642dc6671442b284ddd57048d9fa5b
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08541407B2

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