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

HRID 930833ノート

反応式

HRID 930833 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
100 °C

実験手順

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 the title compound (13.9 g, 45.9 mmol, 76% yield).

後処理

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

出典と根拠

ORDレコード
ord-cf816a7051ad45f6a98ca1e28e58e798
出典データセット
uspto-grants-2016_03
特許番号
US09296741B2

反応ノート

読み込み中…