Methane → 5-Chloro-2-(propan-2-yl)aniline

HRID 924669Notes

Reaction equation

HRID 924669 reaction equation
O.NN.[Cl:4][C:5]1[CH:10]=[CH:9][C:8]([CH:11]([CH3:13])[CH3:12])=[C:7]([N+:14]([O-])=O)[CH:6]=1.C>CO.[Fe](Cl)(Cl)Cl>[Cl:4][C:5]1[CH:10]=[CH:9][C:8]([CH:11]([CH3:13])[CH3:12])=[C:7]([CH:6]=1)[NH2:14]

Participants

6

Reactant 3

HCID 297MethaneHCID 24654Hydrazine hydrate (1:1)HCID 30186644-Chloro-1-(1-methylethyl)-2-nitrobenzene

Product 1

HCID 223794905-Chloro-2-(propan-2-yl)anilineYield 94%

Reagents, catalysts & solvents 2

HCID 24380Iron chloride (FeCl3)CatalystHCID 887MethanolSolvent2×

Procedure

A solution of hydrazine hydrate (1.7 mL, 35.1 mmol) in methanol (12 mL) was added drop wise to a solution of 4-chloro-2-nitro-1-(propan-2-yl)benzene (1.75 g, 8.8 mmol) in methanol (40 mL), in the presence of iron (III) chloride (146 mg, 0.9 mmol) and activated charcoal (146 mg) and the reaction mixture was stirred under reflux for 7 h. The solid was filtered over celite, the filtrate concentrated and purified by flash chromatography (hexane/EtOAc 9/1) to obtain the title compound as a light-pink oil (1.4 g, 94%).

Workup

  1. temperatureunder reflux for 7 h
  2. filtrationThe solid was filtered over celite
  3. concentrationthe filtrate concentrated
  4. custompurified by flash chromatography (hexane/EtOAc 9/1)

Sources & evidence

ORD record
ord-3632d8aebdc64a838bc6cb679d0ad56e
Source dataset
uspto-grants-2016_03
Patent number
US09283224B2

Reaction notes

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