Indole → 5-Methoxy-2-methyl-1H-indole-3-carbaldehyde

HRID 1461437

反応式

HRID 1461437 の反応式
P(Cl)(Cl)(Cl)=O.[CH3:6][O:7][C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[NH:13][C:12]([CH3:17])=[CH:11]2.N1C2C(=CC=CC=2)C=C1.CN([CH:30]=[O:31])C>>[CH3:6][O:7][C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[NH:13][C:12]([CH3:17])=[C:11]2[CH:30]=[O:31]

参加物

5

反応物 4

HCID 798IndoleHCID 6228Dimethylformamide4 回HCID 24813Phosphorus oxychlorideHCID 706425-Methoxy-2-methylindole

生成物 1

HCID 31595805-Methoxy-2-methyl-1H-indole-3-carbaldehyde収率 98%

反応条件

温度
35 °C

実験手順

Phosphorous oxychloride (12.7 ml, 0.136 mol) is added dropwise at 0° C. to dimethylformamide (42.4 ml, 0.544 mol) over 30 minutes. A solution of 5-methoxy-2-methylindole (20 g, 0.124 mol) in 40 ml of DMF is added dropwise over 45 minutes. When 30 ml of the indole solution has been added, it becomes necessary to add 10 ml of DMF to break up the heavy paste which forms. The reaction mixture is then warmed to 35° C. for one hour. After 30 minutes the reaction again becomes too pasty, and 5 ml more of DMF is added. The bath is removed, and 60 g of crushed ice is added quickly to the reaction mixture. The reaction mixture is stirred for 30 minutes followed by addition of 20 ml of water and 40 g of ice. A solution of sodium hydroxide (25 g) in water (200 ml) is added dropwise to the red solution. After the first one-third of this sodium hydroxide solution has been added, the color changes to yellow, and the remainder of the sodium hydroxide solution is added quickly. It is rapidly brought to a boil (100°-120° C.) for 10 minutes, cooled and refrigerated overnight. The solid is filtered and washed four times with cool water. It is dried in a vacuum oven at 50° C. for 22 hours to give 23.0 g (98%) of powdery yellow crystals of pure 5-methoxy-2-methyl-lH-indole-3-carboxaldehyde; mp 190°-191° C.

後処理

  1. customAfter 30 minutes the reaction
  2. customThe bath is removed
  3. addition60 g of crushed ice is added quickly to the reaction mixture
  4. additionfollowed by addition of 20 ml of water and 40 g of ice
  5. additionA solution of sodium hydroxide (25 g) in water (200 ml) is added dropwise to the red solution
  6. additionAfter the first one-third of this sodium hydroxide solution has been added
  7. additionthe color changes to yellow, and the remainder of the sodium hydroxide solution is added quickly
  8. waitIt is rapidly brought to a boil (100°-120° C.) for 10 minutes
  9. temperaturecooled
  10. waitrefrigerated overnight
  11. filtrationThe solid is filtered
  12. washwashed four times with cool water
  13. customIt is dried in a vacuum oven at 50° C. for 22 hours

出典と根拠

ORDレコード
ord-ec766bff0a88493ba38f21d7c11e0e21
出典データセット
uspto-grants-1991_12
特許番号
US05075330

関連ノート

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