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

HRID 268235

반응식

HRID 268235 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

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°.

후처리

  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.)

출처 및 근거

ORD 기록
ord-6cd3a193594c44ef8c4d13d071ee03b1
출처 데이터셋
uspto-grants-1976_03
특허 번호
US03947452

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