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Water → 2-Cyclopropylmethyl-4-methyl-7-nitro-2h-isoquinolin-1-one

HRID 1358255
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HRID 1358255 반응식
[CH3:1][CH:2]1[C:11]2[C:6](=[CH:7][C:8]([N+:12]([O-:14])=[O:13])=[CH:9][CH:10]=2)[C:5](=[O:15])[NH:4][CH2:3]1.[H-].[Na+].[CH:18]1([CH2:21]Br)[CH2:20][CH2:19]1.O>CN(C=O)C>[CH:18]1([CH2:21][N:4]2[CH:3]=[C:2]([CH3:1])[C:11]3[C:6](=[CH:7][C:8]([N+:12]([O-:14])=[O:13])=[CH:9][CH:10]=3)[C:5]2=[O:15])[CH2:20][CH2:19]1
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참가 물질

6

반응물 4

HCID 962WaterHCID 24758Sodium hydrideHCID 81503BromomethylcyclopropaneHCID 181844524-methyl-7-nitro-3,4-dihydro-2H-isoquinolin-1-one

생성물 1

HCID 181844622-Cyclopropylmethyl-4-methyl-7-nitro-2h-isoquinolin-1-one수율 19.5%

시약·촉매·용매 1

HCID 6228
Dimethylformamide
용매

실험 절차

To 4-methyl-7-nitro-3,4-dihydro-2H-isoquinolin-1-one (0.90 g) in DMF (30 ml), sodium hydride (0.212 g, 60% suspension in oil) was added in portions. The mixture was stirred for 1 h then treated with cyclopropylmethyl bromide (0.72 g). The mixture was stirred for 4 h, poured into water and extracted with ethyl acetate. The organic phase was washed with water, dried (Na2SO4) and solvent removed at reduced pressure. The residue was column chromatographed (silica gel, DCM) to give the sub-title compound (0.22 g) as a yellow solid. 1H NMR δ: 0.43-0.54 (4H, m), 1.26 (1H, m), 2.30 (3H, s), 3.84 (2H, d, J 7.2 Hz), 7.70 (1H, s), 7.91 (1H, d, J=9.0 Hz), 8.50 (1H, dd, J=2.5, 8.9 Hz), 8.98 (1H, d, J=2.5 Hz).

후처리

  1. stirringThe mixture was stirred for 4 h
  2. extractionextracted with ethyl acetate
  3. washThe organic phase was washed with water
  4. dry with materialdried (Na2SO4) and solvent
  5. customremoved at reduced pressure
  6. customchromatographed (silica gel, DCM)

출처 및 근거

ORD 기록
ord-62cd87a802da4229ab8c5fd1018542df
출처 데이터셋
uspto-grants-2003_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06596730B1

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