Dimethylformamide → 2-Acetyl-7-methoxy-3-methyl-9-oxo-1,3,4,9-tetrahydropyrrolo[3,4-b]quinoline

HRID 1249760ノート

反応式

HRID 1249760 の反応式
[H-].[Na+].[CH3:3][CH:4]1[C:16]2[NH:15][C:14]3[C:9](=[CH:10][C:11]([O:17][CH3:18])=[CH:12][CH:13]=3)[C:8]=2[CH2:7][CH2:6][N:5]1[C:19](=[O:21])[CH3:20].CN(C=[O:26])C>>[C:19]([N:5]1[CH2:6][C:7]2[C:8](=[O:26])[C:9]3[CH:10]=[C:11]([O:17][CH3:18])[CH:12]=[CH:13][C:14]=3[NH:15][C:16]=2[CH:4]1[CH3:3])(=[O:21])[CH3:20]

参加物

4

反応物 3

HCID 6228DimethylformamideHCID 24758Sodium hydride2 回HCID 18328986HCID 18328986、化合物

生成物 1

HCID 98383642-Acetyl-7-methoxy-3-methyl-9-oxo-1,3,4,9-tetrahydropyrrolo[3,4-b]quinoline収率 45%

実験手順

NaH (1.2 eq; 60% suspension in oil) is added to a solution of 1-methyl-2-acetyl-6-methoxy-1,2,3,4-tetrahydro-β-carboline (1.56 g; 6.0 mmol) in DMF (20 ml). The mixture is stirred under an oxygen atmosphere for 48 hours, further NaH (1.1 eq) is then added and stirring is continued overnight. The DMF is then distilled off under reduced pressure. The crude product is taken up in water and then filtered. Saturated NH4Cl solution is added to the aqueous phase. The mixture is stirred for 30 minutes. The precipitate is filtered off and then washed successively with water, an MeOH/CH2Cl mixture (10/90), acetone and then ethyl acetate. After drying, 2-acetyl-7-methoxy-3-methyl-9-oxo-1,3,4,9-tetrahydropyrrolo[3,4-b]quinoline is obtained (yield=45%).

後処理

  1. stirringstirring
  2. waitis continued overnight
  3. distillationThe DMF is then distilled off under reduced pressure
  4. filtrationfiltered
  5. additionSaturated NH4Cl solution is added to the aqueous phase
  6. stirringThe mixture is stirred for 30 minutes
  7. filtrationThe precipitate is filtered off
  8. washwashed successively with water
  9. customAfter drying

出典と根拠

ORDレコード
ord-e68ba8361a354520bc0875d882399971
出典データセット
uspto-grants-2002_01
特許番号
US06335346B1

反応ノート

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