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

HRID 1358255Notes

Reaction equation

HRID 1358255 reaction equation
[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

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-62cd87a802da4229ab8c5fd1018542df
Source dataset
uspto-grants-2003_07
Patent number
US06596730B1

Reaction notes

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