HCID 22176515, compound → HCID 22176470, compound

HRID 2307269Notes

Reaction equation

HRID 2307269 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[CH:5]=[C:4]([CH2:11][CH3:12])[N+:3]=1[O-]>C(O)(=O)C.[Fe]>[Br:1][C:2]1[CH:7]=[C:6]([NH2:8])[CH:5]=[C:4]([CH2:11][CH3:12])[N:3]=1

Participants

4

Reactant 1

HCID 22176515HCID 22176515, compound

Product 1

HCID 22176470HCID 22176470, compound

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

A solution of 2-bromo-6-ethyl-4-nitro-pyridine 1-oxide (example 5b) (15.9 g, 69 mmol) in acetic acid (310 ml) was treated with powdered iron (25.8 g, 462 mmol). The mixture was slowly heated to 100° C. and kept for 1 hr at this temperature. Then the reaction mixture was cooled to rt and filtered. After evaporation of the solvent the residue was crystallized to yield the title compound as a beige material (88%). Mp. 75-77° C. (pentane), MS: m/e=200 (M+).

Workup

  1. temperatureThen the reaction mixture was cooled to rt
  2. filtrationfiltered
  3. customAfter evaporation of the solvent the residue
  4. customwas crystallized

Sources & evidence

ORD record
ord-a7269623d10b431a89cebff5584cc744
Source dataset
uspto-grants-2004_12
Patent number
US06831087B2

Reaction notes

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