Dimethylformamide → 2-(4-bromobutyl)-1H-benzo[de]isoquinoline-1,3(2H)-dione

HRID 436010

反応式

HRID 436010 の反応式
[CH:1]1[CH:2]=[C:3]2[C:8]3=[C:9]([C:11]([NH:13][C:14](=[O:15])[C:7]3=[CH:6][CH:5]=[CH:4]2)=[O:12])[CH:10]=1.CN(C)C=O.[OH-].[K+].[Br:23][CH2:24][CH2:25][CH2:26][CH2:27]Br>CO>[Br:23][CH2:24][CH2:25][CH2:26][CH2:27][N:13]1[C:14](=[O:15])[C:7]2[CH:6]=[CH:5][CH:4]=[C:3]3[C:8]=2[C:9](=[CH:10][CH:1]=[CH:2]3)[C:11]1=[O:12]

参加物

6

反応物 4

HCID 6228DimethylformamideHCID 80561,4-DibromobutaneHCID 14797Potassium HydroxideHCID 66491Naphthalimide

生成物 1

HCID 27823602-(4-bromobutyl)-1H-benzo[de]isoquinoline-1,3(2H)-dione

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

100 g. (0.5 mole) of 1,8-naphthalimide is suspended in 2100 ml. of dimethylformamide and the mixture is heated to 90° to form a complete solution. A solution of 36.3 g. (0.55 mole) of potassium hydroxide (85%) in 100 ml. of methanol is added resulting in the immediate formation of a yellow precipitate. The resulting mixture is stirred for one hour at 90° and cooled to 25°. 245 g.(1.0 mole) of 1,4-dibromobutane is added and the mixture is again heated to 90° and stirred for an additional hour. A precipitate remains in the mixture but is more granular than the initial material. The reaction mixture is cooled and the precipitate filtered off. The solvent is removed under vacuum and the residue is diluted with 500 ml. of hexane immediately precipitating crude 2-(4-bromobutyl)-1H-benz[de] isoquinoline-1,3 (2H)-dione. The precipitate is filtered off, washed with fresh hexane and dried for 2 hours at 50° (0.1 mm.) to yield 2-(4-bromobutyl)-1H-benz[de] isoquinoline-1,3 (2H)-dione. An analytically pure sample is prepared by dissolving the above product in hot 95% ethanol and recrystallizing by allowing the solution to cool to 25°. The resulting precipitate is dried for two hours at 50° (0.1 mm.) to yield pure 2-(4-bromobutyl)-1H-benz[de] isoquinoline-1,3 (2H)-dione, m.p. 113°-115°.

後処理

  1. customto form a complete solution
  2. customresulting in the immediate formation of a yellow precipitate
  3. temperaturecooled to 25°
  4. temperaturethe mixture is again heated to 90°
  5. stirringstirred for an additional hour
  6. temperatureThe reaction mixture is cooled
  7. filtrationthe precipitate filtered off
  8. customThe solvent is removed under vacuum
  9. additionthe residue is diluted with 500 ml
  10. customof hexane immediately precipitating crude 2-(4-bromobutyl)-1H-benz[de] isoquinoline-1,3 (2H)-dione
  11. filtrationThe precipitate is filtered off
  12. washwashed with fresh hexane
  13. customdried for 2 hours at 50° (0.1 mm.)

出典と根拠

ORDレコード
ord-9e421b22fb5b4aa1bd92ecb0f92d8a53
出典データセット
uspto-grants-1977_02
特許番号
US04007191

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