Sulfuric Acid → Kenpaullone

HRID 498987

反応式

HRID 498987 の反応式
[NH:1]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[C:5](=O)[CH2:4][CH2:3][C:2]1=[O:13].Cl.[Br:15][C:16]1[CH:21]=[CH:20][C:19]([NH:22]N)=[CH:18][CH:17]=1.C([O-])(=O)C.[Na+].S(=O)(=O)(O)O>C(O)(=O)C>[Br:15][C:16]1[CH:17]=[C:18]2[C:4]3[CH2:3][C:2](=[O:13])[NH:1][C:7]4[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=4[C:5]=3[NH:22][C:19]2=[CH:20][CH:21]=1

参加物

6

反応物 4

HCID 1118Sulfuric AcidHCID 121574-Bromophenylhydrazine hydrochlorideHCID 3693982,3,4,5-tetrahydro-1H-1-benzazepine-2,5-dioneHCID 517045Sodium Acetate2 回

生成物 1

HCID 3820Kenpaullone収率 86.3%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

反応条件

温度
70 °C

実験手順

To a suspension of 1H-[1]benzazepin-2,5(3H, 4H)-dione (0.247 g, 1.3 mmol) in acetic acid (5 ml) was added 4-bromophenylhydrazine hydrochloride (0.532 g, 2.3 mmol) and sodium acetate (0.195 g, 2.3 mmol) and stirred under argon. The mixture was heated at 70° C. for 3 hours, then cooled and concentrated sulfuric acid (0.5 ml) added, before heating at 70° C. for a further 3 hours. The slurry was poured into 10% sodium acetate aqueous solution (20 ml) and the precipitate filtered to give the title compound as a cream solid (0.367 g, yield 79.6%), mp>300° C.; 1H-NMR (DMSO-d6, 300 MHz): δ (ppm)=11.82 (s; 1 H), 10.1 (s; 1H), 7.89 (d; 1H), 7.74 (dd; 1H), 7.41-7.36 (m; 2H), 7.30-7.21 (m; 3H), 3.51 (s; 2H).

後処理

  1. temperaturecooled
  2. temperaturebefore heating at 70° C. for a further 3 hours
  3. filtrationthe precipitate filtered

出典と根拠

ORDレコード
ord-8eeb5fd0bebb403193bc6b4eb854ffd4
出典データセット
uspto-grants-2010_08
特許番号
US07767664B2

関連ノート

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