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

Participants

Role	Name	HCID	Charge
Reactant	Water	HCID 962	—
Reactant	Ceric ammonium nitrate	HCID 180504	—
Reactant	2-(4-Methoxy-benzyl)-4,4-dimethyl-7-nitro-3,4-dihydro-2H-isoquinolin-1-one	HCID 21959362	—
Solvent	Acetonitrile	HCID 6342	—
Product	4,4-Dimethyl-7-nitro-3,4-dihydroisoquinolin-1(2H)-one	HCID 14209953	—

Reaction Conditions

Temperature	0 °C

Reaction Steps

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.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08058445B2
Source dataset	uspto-grants-2011_11
ORD ID	ord-edbfe2357e2544ac994df17ac6cc6089
Source note	uspto-grants-2011_11