Diethyl Ether → 5-Aminofuro[3,2-c]pyridin-5-ium 2,4-dinitrobenzenolate

HRID 2389868Notes

Reaction equation

HRID 2389868 reaction equation
[O:1]1[C:9]2[CH:8]=[CH:7][N:6]=[CH:5][C:4]=2[CH:3]=[CH:2]1.[NH2:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][C:13]=1[N+:21]([O-:23])=[O:22].C(OCC)C>C(#N)C>[N+:21]([C:13]1[CH:14]=[C:15]([N+:18]([O-:20])=[O:19])[CH:16]=[CH:17][C:12]=1[O-:11])([O-:23])=[O:22].[NH2:10][N+:6]1[CH:7]=[CH:8][C:9]2[O:1][CH:2]=[CH:3][C:4]=2[CH:5]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 87140O-(2,4-dinitrophenyl)hydroxylamineHCID 12234604Furo[3,2-c]pyridine

Product 1

HCID 866386655-Aminofuro[3,2-c]pyridin-5-ium 2,4-dinitrobenzenolateYield 80.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of furo[3,2-c]pyridine (960 mg, 8.06 mmol) in acetonitrile (5.0 mL) was added 1-(aminooxy)-2,4-dinitrobenzene (1.77 g, 8.89 mmol) at room temperature, and the mixture was stirred at 40° C. for 15 hr. Diethyl ether was added, and the resulting precipitate was collected by filtration and washed with diethyl ether to give the title compound (2.06 g, yield 80%).

Workup

  1. filtrationthe resulting precipitate was collected by filtration
  2. washwashed with diethyl ether

Sources & evidence

ORD record
ord-ba927f20b32b4711b3a6b375b2f4aca5
Source dataset
uspto-grants-2012_09
Patent number
US08273761B2

Reaction notes

Loading…