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ChemicalBook CAS DataBase List N-Phenylhydroxylamine
100-65-2

N-Phenylhydroxylamine synthesis

11synthesis methods
To a dispersion of 180 gm (2.75 gm-atom) of zinc dust in 500 ml of 50% aqueous ethanol, with vigorous stirring, is added 130 ml (156 gm, 1.27 mole) of nitrobenzene. The reaction is initiated by the dropwise addition of an aqueous ammonium chloride solution and can thereafter be maintained at a controllable rate by the cautious addition of the remaining ammonium chloride solution. The reaction temperature rises during this reduction step. Once reflux has subsided, the basic zinc salts are filtered off using a sintered glass funnel. The light green filtrate is cooled in an ice-salt mixture to precipitate the product. The yield is 100 gm (72.2%), m.p. 81°C.
The reduction of 2-methyl-2-nitropropane is carried out in a similar manner at 10-20°C to afford a 68% yield of N-t-butylhydroxylamine (m.p. 60-62°C). 
-

Yield:100-65-2 98%

Reaction Conditions:

with hydrogen;silica-supported platinum;dimethyl sulfoxide;N-butylamine in isopropyl alcohol at 20; under 760.051 Torr; for 1.75 h;Product distribution / selectivity;

Steps:

51
Into a flask, 20 mg of the silica gel platinum catalyst (5% by weight of Pt) [product name: 5% Pt-silica powder "Escat 2351", manufactured by STREM Co., Ltd.] (0.0026 time mole of platinum, relative to nitrobenzene), 2 mL of IPA (isopropyl alcohol), 0.42 mmol of dimethylsulfoxide (30 μL), 0.072 mmol of n-butylamine (7.1 μL) (14 equivalents, relative to platinum weight in the silica gel platinum catalyst) and 2 mmol of various nitroaryl compounds described in the following Table 5 were charged, and then a balloon sealed with hydrogen gas (about 2 L) was attached, and a reaction was carried out under stirring at room temperature for predetermined time under ordinary pressure. After completion of the reaction, 20 μL of the resultant reaction solution was diluted with 10 mL of 2-propanol containing 0.1 M of toluene, and after removal of the catalyst by using a membrane filter, IPA was removed under reduced pressure, and it was analyzed with NMR. The results are summarized in Table 5.

References:

Wako Pure Chemical Industries, Ltd.;National Institute of Advanced Industrial Science and Technology EP2154125, 2010, A1 Location in patent:Page/Page column 23-24

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