Chloride → 3-Formyl-1H-indole-5-carbonitrile

HRID 567815

反応式

HRID 567815 の反応式
[Cl-].[NH:2]1[C:10]2[C:5](=[CH:6][C:7]([C:11]#[N:12])=[CH:8][CH:9]=2)[CH:4]=[CH:3]1.CN(C)[CH:15]=[O:16]>>[CH:15]([C:4]1[C:5]2[C:10](=[CH:9][CH:8]=[C:7]([C:11]#[N:12])[CH:6]=2)[NH:2][CH:3]=1)=[O:16]

参加物

4

反応物 3

HCID 312ChlorideHCID 6228Dimethylformamide2 回HCID 27513Indole-5-carbonitrile

生成物 1

HCID 285043-Formyl-1H-indole-5-carbonitrile収率 84%

実験手順

Phophoyl chloride (4.24 ml, 45.48 mmol) was added dropwise to dimethylformamide (3.52 ml, 45.48 mmol) and stirred for 30 mins at room temperature. A solution of 1H-indole-5-carbonitrile (5.39 g, 37.9 mmol) in dimethylformamide (10 ml) was added dropwise. A solid precipitated, further dimethylformamide (10 ml) was added to aid stirring and the reaction mixture was then stirred at room temperature for 3 hr. Water was s added to quench the reaction mixture which was then stirred for 18 hr. The stirring was stopped and the reaction mixture was left to stand, after 24 hr a pink solid had precipitated in the organic layer. The layers were separated and organic layer filtered, washed with water and dried to give the desired product (5.44 g, 84%). 1H NMR (DMSO) δ 7.60-7.80 (m, 2H), 8.20-8.30 (m, 2H), 10.00 (s, 1H), 12.20-12.35 (s, br, 1H).

後処理

  1. customA solid precipitated
  2. additionfurther dimethylformamide (10 ml) was added to aid
  3. stirringstirring
  4. stirringthe reaction mixture was then stirred at room temperature for 3 hr
  5. additionadded
  6. customto quench the reaction mixture which
  7. stirringwas then stirred for 18 hr
  8. waitthe reaction mixture was left
  9. waitto stand, after 24 hr
  10. customa pink solid had precipitated in the organic layer
  11. customThe layers were separated
  12. filtrationorganic layer filtered
  13. washwashed with water
  14. customdried

出典と根拠

ORDレコード
ord-6b404e5917454a8cb012bc49e79cc1f8
出典データセット
uspto-grants-2001_01
特許番号
US06180627B2

関連ノート

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