Potassium Carbonate → 2,2-Dimethyl-6-nitro-2H-benzo[B][1,4]oxazin-3(4H)-one

Participants

Role	Name	HCID	Charge
Reactant	Potassium Carbonate	HCID 11430	—
Reactant	Propanoic acid, 2-bromo-2-methyl-, ethyl ester	HCID 11745	—
Reactant	2-Amino-4-Nitrophenol	HCID 3613389	—
Solvent	Water	HCID 962	—
Solvent	Dimethylformamide	HCID 6228	—
Solvent	Ethyl Acetate	HCID 8857	—
Product	2,2-Dimethyl-6-nitro-2H-benzo[B][1,4]oxazin-3(4H)-one	HCID 10656631	—

Reaction Conditions

Temperature	70 °C

Reaction Steps

2-Amino-4-nitrophenol (5 g), ethyl 2-bromo-2-methylpropanoate (5.77 mL, 1.2 eq.), and K2CO3 (6.7 g, 1.5 eq.) were suspended in DMF (50 ml). The reaction mixture was heated at 70° C. overnight. The mixture was then diluted with water (200 mL) and EtOAc (150 mL). The EtOAc layer was washed with water (2×150 mL) and evaporated. The residue was purified by Combiflash chromatography (EtOAc in hexanes=10-100%) to give 2,2-dimethyl-6-nitro-2H-benzo[b][1,4]oxazin-3(4H)-one (3.45 g).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09321763B2
Source dataset	uspto-grants-2016_04
ORD ID	ord-df92a5e18c1642ca9ae5e98ad7e2710f
Source note	uspto-grants-2016_04