Ethylene Glycol → 6-Nitro-1,2-dihydroisoquinolin-1-one

HRID 708797ノート

反応式

HRID 708797 の反応式
C[N:2](C)/[CH:3]=[CH:4]/[C:5]1[CH:14]=[C:13]([N+:15]([O-:17])=[O:16])[CH:12]=[CH:11][C:6]=1[C:7](OC)=[O:8].N.C(O)CO>>[N+:15]([C:13]1[CH:14]=[C:5]2[C:6](=[CH:11][CH:12]=1)[C:7](=[O:8])[NH:2][CH:3]=[CH:4]2)([O-:17])=[O:16]

参加物

4

反応物 3

HCID 174Ethylene GlycolHCID 222AmmoniaHCID 87664981(E)-Methyl 2-(2-(dimethylamino)vinyl)-4-nitrobenzoate

生成物 1

HCID 707009796-Nitro-1,2-dihydroisoquinolin-1-one収率 85%

反応条件

温度
140 °C

実験手順

To Intermediate 3B (1.54 g, 6.15 mmol) in a microwave tube was added 8.0 N ammonia in ethylene glycol (7.69 mL, 61.5 mmol). The tube was placed in microwave and heated at 140° C. for 30 min. The reaction mixture was triturated with EtOAc, stored at 0° C. over night. The precipitate was collected to give Intermediate 3C (0.995 g, 5.23 mmol, 85% yield) as a brown solid. The filtrate was washed with water. The organic layer was dried over sodium sulfate. After evaporation of solvent, the crude was triturated with EtOAc to give additional product. 1H NMR (400 MHz, DMSO-d6) δ ppm 11.35 (br. s., 1H) 8.63 (d, J=2.20 Hz, 1H) 8.39 (d, J=8.79 Hz, 1H) 8.19 (dd, J=8.79, 2.20 Hz, 1H) 7.36 (d, J=7.03 Hz, 1H) 6.82 (d, 1H); MS (ESI) m/z: 191.1 (M+H)+.

後処理

  1. customThe reaction mixture was triturated with EtOAc
  2. waitstored at 0° C. over night
  3. customThe precipitate was collected

出典と根拠

ORDレコード
ord-233ece1c319746318debc57332713bfd
出典データセット
uspto-grants-2015_11
特許番号
US09174974B2

反応ノート

読み込み中…