N-(2,2-diethoxyethyl)-3-methoxy-2-nitrobenzamide → 7-methoxy-8-nitroisoquinolin-1(2H)-one

HRID 577487ノート

反応式

HRID 577487 の反応式
C(O[CH:4](OCC)[CH2:5][NH:6][C:7](=[O:19])[C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([O:14][CH3:15])[C:9]=1[N+:16]([O-:18])=[O:17])C>S(=O)(=O)(O)O>[CH3:15][O:14][C:10]1[C:9]([N+:16]([O-:18])=[O:17])=[C:8]2[C:13]([CH:4]=[CH:5][NH:6][C:7]2=[O:19])=[CH:12][CH:11]=1

参加物

3

反応物 1

HCID 86723712N-(2,2-diethoxyethyl)-3-methoxy-2-nitrobenzamide

生成物 1

HCID 867237137-methoxy-8-nitroisoquinolin-1(2H)-one収率 92.4%

試薬・触媒・溶媒 1

HCID 1118Sulfuric Acid溶媒

反応条件

温度
70 °C

実験手順

A mixture of N-(2,2-diethoxyethyl)-3-methoxy-2-nitrobenzamide (296a, 92 g, 0.295 mol) in concentrated sulfuric acid (1 L) was stirred at 70° C. for three hours. After cooling to room temperature, the mixture was slowly poured into ice water (3 L), causing a solid precipitate to form. The precipitate was collected by filtration. The filter cake was washed with water (1 L) and dried to yield 7-methoxy-8-nitroisoquinolin-1(2H)-one (296b, 60 g, 92% yield) as a brown solid. 1H NMR (400 MHz, DMSO-d6) δ 7.92-7.89 (d, J=9.2 Hz, 1H), 7.81-7.79 (d, J=9.2 Hz, 1H), 7.18-7.15 (t, J=6.6 Hz, 1H), 6.66-6.64 (d, J=7.2 Hz, 1H), 3.95 (s, 3H).

後処理

  1. temperatureAfter cooling to room temperature
  2. customto form
  3. filtrationThe precipitate was collected by filtration
  4. washThe filter cake was washed with water (1 L)
  5. customdried

出典と根拠

ORDレコード
ord-92f63782e292472aa0bb5b440c2aa432
出典データセット
uspto-grants-2015_05
特許番号
US09040515B2

反応ノート

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