Nitrogen → N-(6-nitro-2,3-dihydro-1H-inden-5-yl)acetamide

Participants

Role	Name	HCID	Charge
Reactant	Nitrogen	HCID 947	—
Reactant	1,2-Dimethoxyethane	HCID 8071	—
Reactant	Tetraethyltin	HCID 11704	—
Reactant	3-Chloro-7,8-dihydro-6H-indeno[5,6-e][1,2,4]triazine 1-Oxide	HCID 16081320	—
Reactant	HCID 16081324	HCID 16081324	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Product	N-(6-nitro-2,3-dihydro-1H-inden-5-yl)acetamide	HCID 10751392	—

Reaction Conditions

Temperature	85 °C

Reaction Steps

Alternative Preparation of Ethyl-7,8-dihydro-6H-indeno[5,6-e][1,2,4]triazine 1-Oxide (67). Pd(dppf)Cl2 (130 mg, 0.08 mmol) was added under N2 to a N2-purged solution of chloride 21 (350 mg, 1.6 mmol) and SnEt4 (455 mg, 1.9 mmol) in DME (20 mL) and the mixture was stirred at 85° C. for 16 h. The mixture was cooled, the solvent evaporated and the residue purified by chromatography, eluting with 20% EtOAc/pet. ether, to give (i) starting material 21 (148 mg, 42%) and (ii) 1-oxide 67 (84 mg, 25%) as a yellow solid: mp 79-81° C., spectroscopically identical to the sample prepared above.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07989451B2
Source dataset	uspto-grants-2011_08
ORD ID	ord-09a659a891c04074b82287b80d43179b
Source note	uspto-grants-2011_08