4-Chlorobenzoyl chloride → 1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indole-3-carboxaldehyde

HRID 1195885

反応式

HRID 1195885 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7]([CH3:12])=[C:6]2[CH:13]=[O:14].[H-].[Na+].[Cl:17][C:18]1[CH:26]=[CH:25][C:21]([C:22](Cl)=[O:23])=[CH:20][CH:19]=1.C(OCC)(=O)C>CN(C)C=O.O>[Cl:17][C:18]1[CH:26]=[CH:25][C:21]([C:22]([N:8]2[C:9]3[C:5](=[CH:4][C:3]([O:2][CH3:1])=[CH:11][CH:10]=3)[C:6]([CH:13]=[O:14])=[C:7]2[CH3:12])=[O:23])=[CH:20][CH:19]=1

参加物

7

反応物 4

HCID 85014-Chlorobenzoyl chlorideHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 31595805-Methoxy-2-methyl-1H-indole-3-carbaldehyde

生成物 1

HCID 108927871-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indole-3-carboxaldehyde収率 82.6%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
-60 °C

実験手順

To a solution of 5-methoxy-2-methyl-1H-indole-3-carboxaldehyde (20 g, 106 mmol) in 210 ml of dry dimethylformamide is added oil free sodium hydride (2.7 g, 111 mmol). The reaction mixture is stirred for five hours at which time it is cooled to -60° C., and freshly distilled 4-chlorobenzoyl chloride (14.4 ml, 117 mmol) is added dropwise. It is stirred for an additional 10 minutes and worked up by pouring the cold paste into cold ethyl acetate and water. The organic phase is washed once with dilute sodium bicarbonate solution, once again with water, and once with a saturated solution of sodium chloride. It is further dried with magnesium sulfate, filtered, and concentrated in vacuo to a solid which is stirred vigorously with 50 ml of methanol for two hours. The solid is filtered and dried to give 1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indole-3-carboxaldehyde (28.7 g, 82.5%). A portion which is recrystallized from ethyl acetate has a mp of 150.5°-151.5° C.

後処理

  1. stirringIt is stirred for an additional 10 minutes
  2. washThe organic phase is washed once with dilute sodium bicarbonate solution, once again with water
  3. dry with materialIt is further dried with magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo to a solid which
  6. stirringis stirred vigorously with 50 ml of methanol for two hours
  7. filtrationThe solid is filtered
  8. customdried

出典と根拠

ORDレコード
ord-2f2ef95cde954819b682cb23a636311b
出典データセット
uspto-grants-1992_05
特許番号
US05112846

関連ノート

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