1-Bromopropane → 5-Nitro-1-propylindoline

HRID 352335

반응식

HRID 352335 반응식
[H-].[Na+].[N+:3]([C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[NH:11][CH2:10][CH2:9]2)([O-:5])=[O:4].Br[CH2:16][CH2:17][CH3:18]>CN(C=O)C.O.CCOC(C)=O>[N+:3]([C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[N:11]([CH2:16][CH2:17][CH3:18])[CH2:10][CH2:9]2)([O-:5])=[O:4]

참가 물질

7

반응물 3

HCID 78401-BromopropaneHCID 24758Sodium hydrideHCID 362195-Nitroindoline

생성물 1

HCID 98342765-Nitro-1-propylindoline

시약·촉매·용매 3

HCID 962Water용매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

0.51 g (12.79 mmoles) of 60% NaH is added, at 20° C., by portions, to a solution of 2 g (12.18 mmoles) of 5-nitroindoline in 16 ml of anhydrous DMF. After stirring for a further 30 minutes, 2.32 ml (25.58 mmoles) of 1-bromopropane is added dropwise. Stirring is maintained overnight and the reaction mixture is finally diluted with 50 ml of water and 50 ml of AcOEt. After stirring and decanting, the organic phase is successively washed with 25 ml of water and 25 ml of salt water, dried over Na2SO4, filtered and concentrated to dryness under vacuum. The evaporation residue is then purified on a silica column (eluent: Heptane/AcOEt: 9/1). Orange oil.

후처리

  1. stirringStirring
  2. temperatureis maintained overnight
  3. stirringAfter stirring
  4. customdecanting
  5. washthe organic phase is successively washed with 25 ml of water and 25 ml of salt water
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated to dryness under vacuum
  9. customThe evaporation residue is then purified on a silica column (eluent: Heptane/AcOEt: 9/1)

출처 및 근거

ORD 기록
ord-796e6a3fb63845a989e31572ba112b64
출처 데이터셋
uspto-grants-2004_06
특허 번호
US06747024B1

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