Methyl iodide → 6-Chloro-N-(4-ethoxy-2-nitrophenyl)-N-methyl-3-pyridinecarboxamide

HRID 1007204

反応式

HRID 1007204 の反応式
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([C:8]([NH:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][CH2:18][CH3:19])=[CH:13][C:12]=2[N+:20]([O-:22])=[O:21])=[O:9])=[CH:4][CH:3]=1.[CH3:23][O-].[Na+].IC>CN(C=O)C.C(OCC)(=O)C>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([C:8]([N:10]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH2:18][CH3:19])=[CH:13][C:12]=2[N+:20]([O-:22])=[O:21])[CH3:23])=[O:9])=[CH:4][CH:3]=1

参加物

6

反応物 3

HCID 6328Methyl iodideHCID 98401276-Chloro-N-(4-ethoxy-2-nitrophenyl)-3-pyridinecarboxamideHCID 10942334Sodium Methoxide

生成物 1

HCID 99022846-Chloro-N-(4-ethoxy-2-nitrophenyl)-N-methyl-3-pyridinecarboxamide

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒2 回HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of 6-chloro-N-(4-ethoxy-2-nitrophenyl)-3-pyridinecarboxamide (50 mg, 0.155 mmol) in DMF (2 ml) was added sodium methoxide (12 mg, 0.222 mmol) in DMF (1 ml) and the reaction mixture was stirred for 10 min. To the mixture was added iodomethane (22 mg, 0.155 mmol) slowly and the mixture was stirred for at room temperature for 3 h. It was diluted with ethyl acetate and washed with water and brine, dried over anhydrous sodium sulfate, and evaporated. The residue was purified by column chromatography to yield the titled compound as a light brown liquid. 1H NMR (CDCl3): 8.17 (d, J=2.1, 1H), 7.68-7.65 (m, 1H), 7.35 (d, J=2.7, 1H), 7.21 (t, J=7.8, 2H), 7.10-7.06 (m, 1H), 4.08-4.01 (m, 2H), 3.40 (s, 3H), 1.44 (t, J=6.9, 3H).

後処理

  1. stirringthe mixture was stirred for at room temperature for 3 h
  2. washwashed with water and brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customevaporated
  5. customThe residue was purified by column chromatography

出典と根拠

ORDレコード
ord-2e9b5a0cb09742b5b398e9734a4ad3dd
出典データセット
uspto-grants-2004_09
特許番号
US06794397B2

関連ノート

読み込み中…