Hydrochloric Acid → O-(2,4-dinitrophenyl)hydroxylamine

HRID 513031

Reaktionsgleichung

Reaktionsgleichung von HRID 513031
[N+:1]([C:4]1[CH:21]=[C:20]([N+:22]([O-:24])=[O:23])[CH:19]=[CH:18][C:5]=1[O:6][N:7]1C(=O)C2C(=CC=CC=2)C1=O)([O-:3])=[O:2].C(Cl)Cl.O.NN.Cl>CO>[N+:1]([C:4]1[CH:21]=[C:20]([N+:22]([O-:24])=[O:23])[CH:19]=[CH:18][C:5]=1[O:6][NH2:7])([O-:3])=[O:2]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 24654Hydrazine hydrate (1:1)HCID 70363092-(2,4-Dinitrophenoxy)-1H-isoindole-1,3(2H)-dione

Produkt 1

HCID 87140O-(2,4-dinitrophenyl)hydroxylamine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A 5 L four-necked flask equipped with an overhead stirrer, thermocouple and a condenser was charged with 2-(2,4-dinitrophenoxy)isoindoline-1,3-dione (I-36) (96 g, 291.6 mmol) and DCM (2 L). The stirred solution was cooled to 0° C. and a solution of hydrazine hydrate (36.46 g, 729 mol) in MeOH (300 mL) was added at 0° C. The reaction mixture rapidly became bright yellow and a precipitate formed. The suspension was stirred at 0° C. for 2 hours. 0.5 N HCl (2 L) was added at 0° C. and stirred for 30 minutes. The mixture was filtered and washed with DCM (2×200 mL). The organic layer was separated, dried over MgSO4, filtered and the solvent removed to give O-(2,4-dinitrophenyl)hydroxylamine (I-37) as a red-orange solid. 1H NMR (400 MHz, CDCl3) δ 8.82 (d, 1 H), 8.44 (dd, 1 H), 8.07 (d, 1 H), 6.42 (sbr, 2 H).

Aufarbeitung

  1. customA 5 L four-necked flask equipped with an overhead stirrer
  2. customThe reaction mixture rapidly became bright yellow and a precipitate formed
  3. stirringstirred for 30 minutes
  4. filtrationThe mixture was filtered
  5. washwashed with DCM (2×200 mL)
  6. customThe organic layer was separated
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. customthe solvent removed

Quellen und Nachweise

ORD-Eintrag
ord-fc7ca8de90c44828a79dd8c88e18b5fa
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09102671B2

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