Water → 4,4-Dimethyl-7-nitro-3,4-dihydroisoquinolin-1(2H)-one

HRID 238457Notes

Reaction equation

HRID 238457 reaction equation
COC1C=CC(C[N:8]2[CH2:17][C:16]([CH3:19])([CH3:18])[C:15]3[C:10](=[CH:11][C:12]([N+:20]([O-:22])=[O:21])=[CH:13][CH:14]=3)[C:9]2=[O:23])=CC=1.O.O=[N+]([O-])[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[Ce+4].[NH4+].[NH4+]>CC#N>[CH3:18][C:16]1([CH3:19])[C:15]2[C:10](=[CH:11][C:12]([N+:20]([O-:22])=[O:21])=[CH:13][CH:14]=2)[C:9](=[O:23])[NH:8][CH2:17]1

Participants

5

Reactant 3

HCID 962WaterHCID 180504Ceric ammonium nitrateHCID 219593622-(4-Methoxy-benzyl)-4,4-dimethyl-7-nitro-3,4-dihydro-2H-isoquinolin-1-one

Product 1

HCID 142099534,4-Dimethyl-7-nitro-3,4-dihydroisoquinolin-1(2H)-one

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
0 °C

Procedure

2-(4-Methoxy-benzyl)-4,4-dimethyl-7-nitro-3,4-dihydro-2H-isoquinolin-1-one (2.0 g) was dissolved in CH3CN (100 ml) and H2O (50 ml) and cooled to 0° C. CAN (9.64 g) was added and the reaction was stirred at 0° C. for 30 min, then warmed to RT and stirred for 6 h. The mixture was extracted with CH2Cl2 (2×300 ml) washed with sat'd NH4Cl, dried over MgSO4, filtered and concentrated. The crude material was recrystallized in CH2Cl2/EtOAc (1:1) to give 4,4-dimethyl-7-nitro-3,4-dihydro-2H-isoquinolin-1-one as a white solid.

Workup

  1. temperaturewarmed to RT
  2. stirringstirred for 6 h
  3. extractionThe mixture was extracted with CH2Cl2 (2×300 ml)
  4. washwashed with sat'd NH4Cl
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude material was recrystallized in CH2Cl2/EtOAc (1:1)

Sources & evidence

ORD record
ord-32ee099fcd9747b9856a2377819d7cc1
Source dataset
uspto-grants-2014_02
Patent number
US08642624B2

Reaction notes

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