Methyl iodide → 6,7,12,13-Tetrahydro-3,9-dimethoxy-6,12-dimethyl-5,7-dioxo-5H-indolo[2,3-a]-pyrrolo[3,4-c]carbazole

HRID 1586600ノート

反応式

HRID 1586600 の反応式
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]2[NH:9][C:10]3[C:22]4[NH:21][C:20]5[C:15](=[CH:16][C:17]([O:23][CH3:24])=[CH:18][CH:19]=5)[C:14]=4[C:13]4[C:25](=[O:30])[N:26]([CH3:29])[C:27](=[O:28])[C:12]=4[C:11]=3[C:5]=2[CH:4]=1.[H-].[Na+].[CH3:33]I>CN(C)C=O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]2[NH:9][C:10]3[C:22]4[N:21]([CH3:33])[C:20]5[C:15](=[CH:16][C:17]([O:23][CH3:24])=[CH:18][CH:19]=5)[C:14]=4[C:13]4[C:25](=[O:30])[N:26]([CH3:29])[C:27](=[O:28])[C:12]=4[C:11]=3[C:5]=2[CH:4]=1

参加物

5

反応物 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 212168326,7,12,13-tetrahydro-3,9-dimethoxy-6-methyl-5,7-dioxo-5H-indolo[2,3-a]-pyrrolo[3,4-c]carbazole

生成物 1

HCID 212168616,7,12,13-Tetrahydro-3,9-dimethoxy-6,12-dimethyl-5,7-dioxo-5H-indolo[2,3-a]-pyrrolo[3,4-c]carbazole

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

反応条件

温度
20 °C

実験手順

A solution of 1 g (2.5 mmol) 6,7,12,13-tetrahydro-3,9-dimethoxy-6-methyl-5,7-dioxo-5H-indolo[2,3-a]-pyrrolo[3,4-c]carbazole in 50 ml dry dimethylformamide is added dropwise at 20° C. to a suspension of 91 mg (3.0 mmol) sodium hydride (80% in paraffin oil) in 5 ml dimethylformamide under an atmosphere of argon. After stirring for 1 hour at 20° C., 0.2 ml (3.2 mmol) methyl iodide are added thereto and the reaction mixture is stirred for 16 hours at 20° C. It is then evaporated in a vacuum and the residue is partitioned between ethyl acetate and water. The ethyl acetate phase is separated off, dried over anhydrous sodium sulphate, filtered and evaporated. The residue is stirred with 30 ml diisopropyl ether/ethyl acetate (2:1 v/v) and the undissolved product is filtered off. 6,7,12,13-Tetrahydro-3,9-dimethoxy-6,12-dimethyl-5,7-dioxo-5H-indolo[2,3-a]-pyrrolo[3,4-c]carbazole is obtained in the form of a pale brown amorphous powder.

後処理

  1. stirringthe reaction mixture is stirred for 16 hours at 20° C
  2. customIt is then evaporated in a vacuum
  3. customthe residue is partitioned between ethyl acetate and water
  4. customThe ethyl acetate phase is separated off
  5. dry with materialdried over anhydrous sodium sulphate
  6. filtrationfiltered
  7. customevaporated
  8. stirringThe residue is stirred with 30 ml diisopropyl ether/ethyl acetate (2:1 v/v)
  9. filtrationthe undissolved product is filtered off

出典と根拠

ORDレコード
ord-3174b8f6bf794ff2a624e4122855b68d
出典データセット
uspto-grants-1999_08
特許番号
US05945440

反応ノート

読み込み中…