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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1994450Generated: October 30, 2026

Trifluoroacetic acid → Trifluoroacetic acid

https://huagongshe.com/reaction/1994450

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTrifluoroacetic acidHCID 6422—
Reactant1-Fluoro-2-nitrobenzeneHCID 73895—
Reactant1-Fluoro-3-methoxy-2-nitrobenzeneHCID 2782776—
Reactant3-Hydroxy-4-(8-methyl-8-aza-bicyclo[3.2.1]oct-3-ylamino)-benzoic acid methyl esterHCID 59814678—
Reactant3-Hydroxy-4-(8-methyl-8-aza-bicyclo[3.2.1]oct-3-ylamino)-benzonitrileHCID 59814698—
ProductTrifluoroacetic acidHCID 6422—
Product6-Methoxy-10-(8-methyl-8-aza-bicyclo[3.2.1]oct-3-yl)-10H-phenoxazine-3-carbonitrileHCID 59814735—

Reaction Steps

Using an adaptation of Procedure 2, substituting the TFA salt of 3-hydroxy-4-(8-methyl-8-aza-bicyclo[3.2.1]oct-3-ylamino)-benzonitrile, 2p for the TFA salt of 3-hydroxy-4-(8-methyl-8-aza-bicyclo[3.2.1]oct-3-ylamino)-benzoic acid methyl ester, 1a, and 1-fluoro-3-methoxy-2-nitrobenzene, 1e for 2-fluoronitrobenzene, the title compound 6-methoxy-10-(8-methyl-8-aza-bicyclo[3.2.1]oct-3-yl)-10H-phenoxazine-3-carbonitrile, 3p was obtained as TFA salt and as a mixture of endo and exo isomers after purification via reverse phase HPLC (eluent gradient: 20% to 45% CH3CN in water containing 0.1% TFA). MS m/z=362 (M+1).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07652005B2
Source datasetuspto-grants-2010_01
ORD IDord-24029bed7cf84186a1b7d747051f0778
Source noteuspto-grants-2010_01