2,2'-OXYDIANILINE

General procedure: A suspension of iron powder and HCl in water was stirred and refluxed for 25 min. Then, the corresponding dinitro compound was added to this hot suspension and the mixture was refluxed for 24 h. The mixture was allowed to reach room temperature and hydrolyzed with 20 mL of NaOH 2.5 M and, extracted with chloroform (2 20 mL). The organic phase was dried with Na2SO4 and evaporated to yield the diamino compounds as solids.In a 50 ml reaction flask by adding 2- fluoro-nitrobenzene (7.06 mg, 0 . 05mmol), pinacone ester boric acid (12.7 mg, 0 . 05mmol), copper chloride (0.68 mg, 10percent * 0.05mmol), 1, 2(Diphenylphosphino) ethane(2.00 mg, 10percent * 0.05mmol), potassium carbonate (2.76 mg, 40percent * 0.05mmol). DMF added in the reaction solvent, the reaction temperature 140 °C, the reaction time is 10h, is dissolved with water to produce a dark brown solution, then using ethyl acetate extraction, the solution of the ethyl acetate layer reservations, hangs does, then using the 200 - 300 mesh silica gel column separation (elution agent is 1:1 of dichloromethane/hexane), after removing the solvent, to obtain 2 - nitro -2 ' - phenylaniline ether, the structural formula:EXAMPLE II OBBA (1.20 g, 4.62 mmole) and hydroxylamine hydrochloride (0.77 g, 11.1 mmole) were placed in a round bottom flask with 11.3 g of polyphosphoric acid. The flask was filled with nitrogen and kept under a slow stream of nitrogen. After 10 min at 160 C., the contents of the flask were poured into 50 g of crushed ice and basified with 20% KOH to pH 7. After stirring for 2 hours at room temperature, enough concentrated phosphoric acid was added so that the pH was less than 5. This solution was filtered, then basified again with 20% KOH to precipitate 0.83 g of crystalline oxybisaniline, 89% yield, based on OBBA.EXAMPLE IV The procedure of Example II was repeated, using OBBA (1.50 g, 5.81 mmole), hydroxylammonium phosphate (0.84 g, 4.26 mmole) and 15 g of polyphosphoric acid. Oxybisaniline was isolated in 87% yield, based on OBBA, M.P. 190-192 C. Hydroxylammonium phosphate accordingly is an acceptable form of a hydroxylamine for this reaction.EXAMPLE I Oxybisbenzoic acid (OBBA) (0.97 g, 3.76 mmole) and hydroxylamine hydrochloride (0.59 g, 8.5 mmole) were placed in a 3-neck round bottom flask with 10.5 g of polyphosphoric acid. The flask was stirred mechanically and heated to 160 C. After 15 min. at 160 C., the contents of the flask were poured into 50 g of crushed ice, then filtered. The filtrate was basified with enough 20% KOH to bring it to pH 7. This solution was then filtered to give 0.40 g of tan crystals, m.p.=183-185 C., 53% yield based on OBBA. The product was identified as oxybisaniline by comparison with an authentic sample. The melting point of 99+% pure OBA is 190-192 C.

Molecular Weight:200.24
XLogP3:1.8
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:2
Exact Mass:200.094963011
Monoisotopic Mass:200.094963011
Topological Polar Surface Area:61.3
Heavy Atom Count:15
Complexity:178
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes