Methane → HCID 12465045, compound

HRID 925419Notes

Reaction equation

HRID 925419 reaction equation
O.NN.[Cl:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH3:12])=[C:7]([N+:13]([O-])=O)[CH:6]=1.C>CO.[Fe](Cl)(Cl)Cl>[Cl:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH3:12])=[C:7]([CH:6]=1)[NH2:13]

Participants

6

Reactant 3

HCID 297MethaneHCID 24654Hydrazine hydrate (1:1)HCID 15892659HCID 15892659, compound

Product 1

HCID 12465045HCID 12465045, compoundYield 97.1%

Reagents, catalysts & solvents 2

HCID 24380Iron chloride (FeCl3)CatalystHCID 887MethanolSolvent2×

Procedure

A solution of hydrazine hydrate (6.95 mL, 134.7 mmol) in MeOH (50 mL) was added dropwise to a solution of 4-chloro-1-ethyl-2-nitrobenzene (6.25 g, 33.7 mmol) in MeOH (120 mL), in the presence of iron(III) chloride (547 mg, 3.4 mmol) and activated charcoal (547 mg), and the reaction mixture was stirred under reflux for 13 h. The solids were filtered over celite, the filtrate concentrated and purified by flash chromatography (hexane:AcOEt 9:1) to obtain the title compound as a light-pink oil (5.09 g, 97%).

Workup

  1. temperatureunder reflux for 13 h
  2. filtrationThe solids were filtered over celite
  3. concentrationthe filtrate concentrated
  4. custompurified by flash chromatography (hexane:AcOEt 9:1)

Sources & evidence

ORD record
ord-7fbaee9182254e76ad42f72b84435fe1
Source dataset
uspto-grants-2016_03
Patent number
US09284298B2

Reaction notes

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