Water → 5-Bromo-4-[2-(dimethylamino)ethenyl]-2-methoxy-3-nitropyridine

HRID 632737노트

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HRID 632737 반응식
[Br:1][C:2]1[C:3]([CH3:13])=[C:4]([N+:10]([O-:12])=[O:11])[C:5]([O:8][CH3:9])=[N:6][CH:7]=1.C[O-].[Li+].CO[CH:19](OC)[N:20]([CH3:22])[CH3:21].O>CN(C)C=O>[Br:1][C:2]1[C:3](/[CH:13]=[CH:19]/[N:20]([CH3:22])[CH3:21])=[C:4]([N+:10]([O-:12])=[O:11])[C:5]([O:8][CH3:9])=[N:6][CH:7]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 78373Dimethylformamide dimethyl acetalHCID 4177230Lithium methanolateHCID 407869095-Bromo-2-methoxy-3-nitro-4-picoline

생성물 1

HCID 578831255-Bromo-4-[2-(dimethylamino)ethenyl]-2-methoxy-3-nitropyridine수율 76%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
100 °C

실험 절차

5-Bromo-2-methoxy-4-methyl-3-nitropyridine (15.0 g, 60.7 mmol) was dissolved in dimethylformamide (300 mL), and lithium methanolate (6.07 mL, 6.07 mmol, 1 M) was added. The reaction mixture was heated to 100° C. To this mixture was added 1,1-dimethoxy-N,N-dimethylmethanamine (64.5 mL, 486 mmol) over 10 minutes. The reaction mixture was stirred at 95° C. for 16 hours. The reaction mixture was cooled to room temperature and water was added carefully (300 mL, exothermic). The resulting precipitate was collected by vacuum filtration, washed with water, and dried to provide (E)-2-(5-bromo-2-methoxy-3-nitropyridin-4-yl)-N,N-dimethylethenamine (13.9 g, 45.9 mmol, 76% yield).

후처리

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationThe resulting precipitate was collected by vacuum filtration
  3. washwashed with water
  4. customdried

출처 및 근거

ORD 기록
ord-6464814717f34c899d589c684c1a822f
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09321765B2

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