2-Bromopyridine → 4-cyano-2-nitro-N-(2-pyridyl)aniline

HRID 382555

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HRID 382555 반응식
[C:1]([C:3]1[CH:9]=[CH:8][C:6]([NH2:7])=[C:5]([N+:10]([O-:12])=[O:11])[CH:4]=1)#[N:2].Br[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=1.C(=O)([O-])[O-].[K+].[K+]>[N+](C1C=CC=CC=1)([O-])=O>[C:1]([C:3]1[CH:9]=[CH:8][C:6]([NH:7][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=2)=[C:5]([N+:10]([O-:12])=[O:11])[CH:4]=1)#[N:2]

참가 물질

5

반응물 3

HCID 79732-BromopyridineHCID 11430Potassium CarbonateHCID 5959014-Amino-3-nitrobenzonitrile

생성물 1

HCID 227367144-cyano-2-nitro-N-(2-pyridyl)aniline수율 46%

시약·촉매·용매 1

HCID 7416Nitrobenzene용매

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온도
200 °C

실험 절차

A mixture of 4-cyano-2-nitroaniline (10.8 g, 66 mmol), 2-bromopyridine (12.6 g, 80 mmol), anhydrous potassium carbonate (9.12 g, 66 mmol) and copper-bronze (1.0 g, 15.7 mmol) in nitrobenzene (100 ml) was heated overnight at 200° C. The reaction mixture was cooled and filtered through a pad of celite. The filter cake was washed with dichloromethane (500 ml) and the filtrate was evaporated. The resultant residue was purified by column chromatography (silica gel, 500 g; n-hexane/ethyl acetate/dichloromethane (4/1/1)) to afford 7.28 g (46%) of 4-cyano-2-nitro-N-(2-pyridyl)aniline as orange solids.

후처리

  1. temperatureThe reaction mixture was cooled
  2. filtrationfiltered through a pad of celite
  3. washThe filter cake was washed with dichloromethane (500 ml)
  4. customthe filtrate was evaporated
  5. customThe resultant residue was purified by column chromatography (silica gel, 500 g; n-hexane/ethyl acetate/dichloromethane (4/1/1))

출처 및 근거

ORD 기록
ord-1ff60099c07447808b1dd7af31b144b0
출처 데이터셋
uspto-grants-2001_10
특허 번호
US06310079B1

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