Sodium Hydroxide → 2,3-Dihydro-7-methyl-6-nitroindole

HRID 1275648

反応式

HRID 1275648 の反応式
[CH3:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[NH:9][CH2:8][CH2:7]2.[N+:11]([O-:14])([O-:13])=[O:12].[K+].[OH-].[Na+]>S(=O)(=O)(O)O>[CH3:1][C:2]1[C:3]([N+:11]([O-:13])=[O:12])=[CH:4][CH:5]=[C:6]2[C:10]=1[NH:9][CH2:8][CH2:7]2.[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([N+:11]([O-:14])=[O:12])=[C:6]2[C:10]=1[NH:9][CH2:8][CH2:7]2

参加物

6

反応物 3

HCID 14798Sodium HydroxideHCID 24434Potassium NitrateHCID 123777887-Methyl-2,3-dihydro-1H-indole

生成物 2

HCID 158963682,3-Dihydro-7-methyl-6-nitroindole収率 1,762.8%HCID 158963697-Methyl-4-nitro-indoline収率 96%

試薬・触媒・溶媒 1

HCID 1118Sulfuric Acid溶媒

反応条件

温度
0 °C

実験手順

Concentrated sulfuric acid (270 mL) is added to 2,3-dihydro-7-methylindole (10.2 g, 76.6 mol) and the solution is cooled to approximately 0° C. using an ice water bath. Solid potassium nitrate (8.52 g, 8.43 mmol) is slowly added to this solution while maintaining the temperature of the reaction below 25° C. After stirring for 1.5 hours, the reaction mixture is poured into a 1000-mL beaker packed with ice. The solution is cautiously basified with 50% NaOH solution and extracted with three 250-mL portions of chloroform. The fractions are combined and dried over anhydrous potassium carbonate. The chloroform is removed by rotary evaporation yielding 13.24 g of 2,3-dihydro-7-methyl-6-nitroindole and 2,3-dihydro-7-methyl-4-nitroindole as a bright orange solid (96% yield). The solid is carried on without further purification.

後処理

  1. temperaturewhile maintaining
  2. customthe temperature of the reaction below 25° C
  3. additionthe reaction mixture is poured into a 1000-mL
  4. extractionextracted with three 250-mL portions of chloroform
  5. dry with materialdried over anhydrous potassium carbonate
  6. customThe chloroform is removed by rotary evaporation

出典と根拠

ORDレコード
ord-623148ddc690464fba6d48a8297d4d96
出典データセット
uspto-grants-2000_12
特許番号
US06162818

関連ノート

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