Hydrogen Peroxide → HCID 135899516, compound

HRID 1669151Notes

Reaction equation

HRID 1669151 reaction equation
[OH:1]O.[N+:3]1([O-:17])[C:8]2[CH:9]=[C:10]3[CH2:15][CH2:14][O:13][C:11]3=[CH:12][C:7]=2[N:6]=[C:5]([NH2:16])[N:4]=1>CC(O)=O>[N+:3]1([O-:17])[C:8]2[CH:9]=[C:10]3[CH2:15][CH2:14][O:13][C:11]3=[CH:12][C:7]=2[N+:6]([O-:1])=[C:5]([NH2:16])[N:4]=1

Participants

4

Reactant 2

HCID 784Hydrogen PeroxideHCID 25140915HCID 25140915, compound

Product 1

HCID 135899516HCID 135899516, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
50 °C

Procedure

H2O2 (70%, 1.2 mL, ca. 24.5 mmol) was added dropwise to a stirred solution of 1-oxide 204 (500 mg, 2.45 mmol) in HOAc (10 mL) and the solution stirred at 50° C. for 24 h. The solution was cooled to 0° C. and the precipitate filtered. The solid was recrystallised from DMF to give 1,4-dioxide 205 (199 mg, 37%) as a red solid: mp>300° C. (235-240° C. dec.); 1H NMR [(CD3)2SO] δ 8.06 (t, J=1.6 Hz, 1H, H-9), 7.86 (br s, 2H, NH2), 7.23 (s, 1H, H-5), 4.77 (t, J=8.3 Hz, 2H, H-8), 3.30-3.60 (m, 2H, H-7); HRMS calcd for C9H8N4O3 (M+) m/z 220.0596, found 220.0601.

Workup

  1. temperatureThe solution was cooled to 0° C.
  2. filtrationthe precipitate filtered
  3. customThe solid was recrystallised from DMF

Sources & evidence

ORD record
ord-d7b83d3982ef430db3adf168ecdb2e23
Source dataset
uspto-grants-2011_08
Patent number
US07989451B2

Reaction notes

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