Dimethylformamide dimethyl acetal → N,N-Dimethyl-2-(2-acetylamino-5-nitropyridin-4-yl)ethenamine

HRID 2393441ノート

反応式

HRID 2393441 の反応式
[C:1]([NH:4][C:5]1[CH:10]=[C:9]([CH3:11])[C:8]([N+:12]([O-:14])=[O:13])=[CH:7][N:6]=1)(=[O:3])[CH3:2].CO[CH:17](OC)[N:18]([CH3:20])[CH3:19]>CN(C=O)C>[CH3:17][N:18]([CH3:20])[CH:19]=[CH:11][C:9]1[C:8]([N+:12]([O-:14])=[O:13])=[CH:7][N:6]=[C:5]([NH:4][C:1](=[O:3])[CH3:2])[CH:10]=1

参加物

4

反応物 2

HCID 78373Dimethylformamide dimethyl acetalHCID 13567013N-(4-methyl-5-nitropyridin-2-yl)acetamide

生成物 1

HCID 53811652N,N-Dimethyl-2-(2-acetylamino-5-nitropyridin-4-yl)ethenamine収率 76.2%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
90 °C

実験手順

To a solution of 2-acetylamino-4-methyl-5-nitropyridine (33.8 g, 0.173 mol) in dry DMF (300 mL) was added dimethylformamide dimethyl acetal (50.7 mL, 0.381 mol) and the mixture heated at 90° C. for 90 min. The solvent was evaporated in vacuo using toluene as an azeotrope. The residue was triturated with ether and the solid collected by filtration to give the title compound (33 g, 76%) as an orange solid. mp 193°-196° C. 1H NMR (250 MHz, CDCl3) δ 2.23 (3H, s), 3.04 (6H, s), 6.12 (1H, d, J=13.1Hz), 7.43 (1H, d, J=13.1Hz), 8.17 (1H, br s), 8.27 (1H, s) and 8.83 (1H, s).

後処理

  1. customThe solvent was evaporated in vacuo
  2. customThe residue was triturated with ether
  3. filtrationthe solid collected by filtration

出典と根拠

ORDレコード
ord-9dbf4cbab6ee4efca335239cf1642829
出典データセット
uspto-grants-1998_09
特許番号
US05807857

反応ノート

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