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Pyridine → N-(5-methylpyridin-2-yl)-2-nitrobenzamide

HRID 269722
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HRID 269722 반응식
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][N:3]=1.N1C=CC=CC=1.[N+:15]([C:18]1[CH:26]=[CH:25][CH:24]=[CH:23][C:19]=1[C:20](Cl)=[O:21])([O-:17])=[O:16]>ClCCl>[N+:15]([C:18]1[CH:26]=[CH:25][CH:24]=[CH:23][C:19]=1[C:20]([NH:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][N:3]=1)=[O:21])([O-:17])=[O:16]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 1049PyridineHCID 118752-Nitrobenzoyl chlorideHCID 153482-Amino-5-methylpyridine

생성물 1

HCID 840320N-(5-methylpyridin-2-yl)-2-nitrobenzamide수율 52.3%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a stirring solution of 2-amino-5-methylpyridine (3.1 g, 29 mmol) in dichloromethane (200 mL) was added pyridine (7.3 mL, 90 mmol) followed by 2-nitrobenzoyl chloride (5.7 g, 30 mmol). After 4 h, the solvent was removed in vacuo and the residue was partitioned between ethyl acetate (500 mL) and water (250 mL). The organic phase was separated and washed with water, brine, dried (MgSO4) and filtered, and then concentrated in vacuo to a volume of about 100 mL (precipitate observed). The mixture was then sonicated and allowed to stand overnight then filtered. The collected solid was then washed with diethyl ether, filtered and dried under vacuum to give 3.9 g (52%) of the title compound.

후처리

  1. customthe solvent was removed in vacuo
  2. customthe residue was partitioned between ethyl acetate (500 mL) and water (250 mL)
  3. customThe organic phase was separated
  4. washwashed with water, brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo to a volume of about 100 mL (precipitate observed)
  8. customThe mixture was then sonicated
  9. waitto stand overnight
  10. filtrationthen filtered
  11. washThe collected solid was then washed with diethyl ether
  12. filtrationfiltered
  13. customdried under vacuum

출처 및 근거

ORD 기록
ord-5d926ab8217a4626b66edd9e0faf98cb
출처 데이터셋
uspto-grants-2008_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07449457B2

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