ChemicalBook CAS DataBase List O-(2,4-dinitrophenyl)hydroxylamine

O-(2,4-dinitrophenyl)hydroxylamine synthesis

7synthesis methods

Product Name:O-(2,4-dinitrophenyl)hydroxylamine
CAS Number:17508-17-7
Molecular formula:C6H5N3O5
Molecular Weight:199.12

To a stirred solution of 13.3 gm (0.1 mole) of t-butyl JV-hydroxycar-bamate and 5.6 gm (0.1 mole) of potassium hydroxide in 200 ml of absolute ethanol is added 20.2 gm (0.1 mole) of 2,4-dinitrochlorobenzene. The resultant deep red solution is stirred at room temperature for 1 hr; then enough glacial acetic acid is added dropwise to produce a light yellow solution. The solution is poured into 1.5 liters of cold water. The yellow oil which separates is gradually converted to crystals. The solid ?-butyl JV-(2,4-dinitrophenoxy)carbamate is separated, dried, and recrystallized from an ethyl acetate-hexane mixture to afford 16.4 gm (53%), m.p. 74-75°C. To 15 ml of trifluoroacetic acid is added 4 gm (0.0133 mole) of the i-butyl J/V-(2,4-dinitrophenoxy)carbamate. After the evolution of carbon dioxide has subsided, the solution is poured into 100 ml of ice water. The resultant oily layer crystallizes on standing to afford 2.5 gm (95%), m.p. 112°C (from ethanol).
Preparation of O-(2,4-Dinitrophenyl)hydroxylamine-1

Preparation of O-(2,4-Dinitrophenyl)hydroxylamine-1

Recently it was discovered that the alkylation of ethyl JV-hydroxy-carbamate under alkaline conditions, particularly in a DMF medium at 60°C in the presence of sodium bicarbonate, leads to the ultimate formation of O-alkylated hydroxylamines. On the other hand, at 80-85°C, the direct alkylation without the presence of a base ultimately leads to N-alkylhydrox-ylamines (see Table I) [59]. The reaction of ethylazidoformate with an alcohol, while perhaps hazardous, may have some merit (Eqs. 31-33). The overall yield, based on ethyl chloroformate, is said to be on the order of 60%.
Preparation of O-(2,4-Dinitrophenyl)hydroxylamine-2

Preparation of O-(2,4-Dinitrophenyl)hydroxylamine-2

2-(2,4-DINITRO-PHENOXY)-ISOINDOLE-1,3-DIONE

60506-35-6
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$65.00/500mg

17508-17-7
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$5.00/250mg

Yield:17508-17-7 98%

Reaction Conditions:

with hydrazine hydrate in dichloromethane at 0; for 4 h;

Steps:

Preparation of Compound 1-2
Preparation of Compound 1-2 2- (2,4-nitrophenoxy) isoindoline-1,3-dione 17.74g (53.88m) and then hydrazine mono-hydrate in yujihan state to 0 dissolved in dichloromethane 350 7.6 (157.33m after the addition of ) was stirred for 4 hours. When the reaction was completed, the reaction mixture poured into a 1N HCl at 0 stirred and the resulting solid was then filter. Filter the solids are washed with MeCN and the filtrate extracted with MC and the organic layer to obtain the desired compound 1-2 10.50g (98%) and dried over MgSO4

References:

Heesung Material Co., Ltd;Jeong, Sujin;Kim, Gi -Yong;Hong, Jang Mi;Yum, Song Jin;Lee, Ju Dong;Jong, Jong-Han;Kim, Min jin;Noh, Young-Seok KR101551895, 2015, B1 Location in patent:Paragraph 0171-0172; 0180-0181

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54322-32-6 Synthesis