Chlorosuccinimide → 4-Chlorosampangine

HRID 260764ノート

反応式

HRID 260764 の反応式
[Cl:1]N1C(=O)CCC1=O.[CH:9]1[CH:10]=[CH:11][C:12]2[C:25](=[O:26])[C:24]3[C:16]4[C:17]([CH:21]=[CH:22][N:23]=3)=[CH:18][CH:19]=[N:20][C:15]=4[C:13]=2[CH:14]=1>CN(C=O)C>[CH:9]1[CH:14]=[C:13]2[C:15]3[C:16]4[C:24]([C:25](=[O:26])[C:12]2=[CH:11][CH:10]=1)=[N:23][CH:22]=[C:21]([Cl:1])[C:17]=4[CH:18]=[CH:19][N:20]=3

参加物

4

反応物 2

HCID 31398ChlorosuccinimideHCID 3871957H-Naphtho(1,2,3-ij)(2,7)naphthyridin-7-one

生成物 1

HCID 100385854-Chlorosampangine収率 53.2%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
100 °C

実験手順

N-Chlorosuccinimide (200 mg, 1.5 mmol) was added to a suspension of sampan-gine (232 mg, 1.0 mmol) in DMF (10 mL) and the mixture stirred at 100° C. for 24 h. The reaction was then poured onto H2O (100 mL) and the solids isolated by filtration. The crude product was purified by column chromatography eluting with CHCl3 /EtOAc (9:1) to give 4-chlorosampangine (21) (142 mg, 53%). Crystallization from EtOAc provided an analytical sample: mp 262°-263° C.; IR (KBr) 1670, 1590, 1410, 1315, 1278, 1240, 1230, 1000, 790, 758, 725, 610 cm1 ; 1H NMR (CDCl3) δ7.68 (ddd, 1 H, J=7.6, 7.6, 1.4 Hz), 7.81 (ddd, 1 H, J= 7.6, 7.6, 1.4 Hz), 7.95 (d, 1 H, J=5.9 Hz), 8.41 (dd, 1 H, J=7.6, 1.4 Hz), 8.76 (dd, 1 H, J=7.6, 1.4 Hz), 8.93 (d, 1H,J=5.9 Hz), 9.09 (s, 1H); 13C NMR (CDCl3) 115.7 (1), 120.0 (0), 125.6 (1), 128.5 (1), 131.7 (1), 132.0 (0), 132.2 (0), 134.8 (1), 135.0 (0), 136.9 (0), 146.0 (0), 147.2 (1), 148.2 (1), 151.5 (0), 181.2 (0) ppm; Anal. calcd for C15H7ClN2O: C 67.56, H 2.65, N 10.50; found C 67.63, H 2.52, N 10.54.

後処理

  1. additionThe reaction was then poured onto H2O (100 mL)
  2. customthe solids isolated by filtration
  3. customThe crude product was purified by column chromatography
  4. washeluting with CHCl3 /EtOAc (9:1)

出典と根拠

ORDレコード
ord-093c3ab8fc9e4e87bbcf512cbb740a24
出典データセット
uspto-grants-1996_06
特許番号
US05530004

反応ノート

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