2-(4-Methoxy-benzyl)-4,4-dimethyl-7-nitro-3,4-dihydro-2H-isoquinolin-1-one → 4,4-Dimethyl-7-nitro-3,4-dihydroisoquinolin-1(2H)-one

HRID 1947645Notes

Reaction equation

HRID 1947645 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.[N+]([O-])([O-])=O.[NH4+].[Ce]>C(#N)C.O>[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 2

HCID 219593622-(4-Methoxy-benzyl)-4,4-dimethyl-7-nitro-3,4-dihydro-2H-isoquinolin-1-oneHCID 57418452Ammonium cerium-nitrate

Product 1

HCID 142099534,4-Dimethyl-7-nitro-3,4-dihydroisoquinolin-1(2H)-oneYield 39%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

A solution of 2-(4-methoxy-benzyl)-4,4-dimethyl-7-nitro-3,4-dihydro-2H-isoquinolin-1-one (1.2 g, 3.52 mmol) and cerium ammonium nitrate (5.78 g, 10.56 mmol) in acetonitrile (30 ml) and water (15 ml) was stirred at 0° C. for 1 hrs, after this time the reaction was warmed to room temperature and stirred for a further 15 h. The solvent was evaporated in vacuo and dichloromethane added. The organic phase was separated, washed with saturated aqueous ammonium chloride solution and brine, then dried and evaporated in vacuo. The crude residue was purified by flash column chromatography (15% ethyl acetate in dichloromethane) to afford the title compound (300 mg, 39%). HPLC retention time 3.71 min. Mass spectrum (ES+) m/z 221 (M+H).

Workup

  1. customThe solvent was evaporated in vacuo and dichloromethane
  2. additionadded
  3. customThe organic phase was separated
  4. washwashed with saturated aqueous ammonium chloride solution and brine
  5. customdried
  6. customevaporated in vacuo
  7. customThe crude residue was purified by flash column chromatography (15% ethyl acetate in dichloromethane)

Sources & evidence

ORD record
ord-14bec4d74fb849eebf588ba3d02fbf02
Source dataset
uspto-grants-2013_03
Patent number
US08399481B2

Reaction notes

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