Potassium Carbonate → 2-Nitroaniline

HRID 922820Notes

Reaction equation

HRID 922820 reaction equation
Cl.[NH2:2]O.C([O-])(=O)C.[Na+].[H][H].F[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[N+:18]([O-:20])=[O:19].C(=O)([O-])[O-].[K+].[K+]>C(O)C.C(O)(=O)C.CN(C=O)C.[Pt]=O>[N+:18]([C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1[NH2:2])([O-:20])=[O:19]

Participants

10

Reactant 5

HCID 11430Potassium CarbonateHCID 738951-Fluoro-2-nitrobenzeneHCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 178418361HCID 178418361, compound

Product 1

HCID 69462-Nitroaniline

Reagents, catalysts & solvents 4

HCID 82844Platinum oxide (PtO)CatalystHCID 176Acetic AcidSolventHCID 702EthanolSolventHCID 6228DimethylformamideSolvent

Procedure

In an alternative procedure, the intermediate can be converted to the oxime using hydroxylamine hydrochloride and sodium acetate in ethanol, and the oxime reduced to 8-exo bicyclo[3.3.1]non-3-yl-8-endo-aza-bicyclo[3.2.1]oct-3-ylamine (RA′) by hydrogenation using platinum oxide in acetic acid under 5 atmospheres of hydrogen. Intermediate (RA′) can be reacted with 2-fluoro nitrobenzene and potassium carbonate in DMF to give 8-exo-bicyclo[3.3.1]non-3-yl-8-endo-aza-bicyclo[3.2.1]oct-3-yl)-(2-nitro-phenyl)-amine (RA″). Finally reduction of the nitro group using 10% palladium on charcoal can give N-(exo-8-bicyclo[3.3.1]non-3-yl-8-endo-aza-bicyclo[3.2.1]oct-3-yl)benzene-1,2-diamine (RB).

Sources & evidence

ORD record
ord-8d2dbc27fd4f4e7f809811f0e0fcc010
Source dataset
uspto-grants-2016_03
Patent number
US09278967B2

Reaction notes

Loading…