6-Chloro-3-nitropyridin-2-ylamine → HCID 85766671, compound

HRID 1799590Notes

Reaction equation

HRID 1799590 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([NH2:8])[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][CH:3]=1.C(O)(=O)C.C(O)(=O)C.IC1C=CC=CC=1>CC(C)=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6](=[N:8][O:10][N+:9]=2[O-:11])[N:7]=1

Participants

4

Reactant 2

HCID 27240356-Chloro-3-nitropyridin-2-ylamineHCID 12217721Iodo benzene diacetate

Product 1

HCID 85766671HCID 85766671, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
80 °C

Procedure

6-Chloro-3-nitropyridin-2-amine (1.25 g, 7.06 mmol) and iodobenzene diacetate (5.80 g, 17.65 mmol) were taken-up in acetone (70.6 ml) and stirred at 80° C. for 6 hours. The reaction was then concentrated directly, and the resulting crude product was purified by silica gel chromatography (0-100% ethyl acetate/hexanes) to afford 5-chloro[1,2,5]oxadiazolo[3,4-b]pyridine 1-oxide. LRMS (APCI) calc'd for (C5H3ClN3O2) [M+H]+, 172. found 172.

Workup

  1. concentrationThe reaction was then concentrated directly
  2. customthe resulting crude product was purified by silica gel chromatography (0-100% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-77c2e6050ac8483baa4477833a1c2616
Source dataset
uspto-grants-2013_01
Patent number
US08344144B2

Reaction notes

Loading…