Water → HCID 12465045, compound

HRID 1773544Notes

Reaction equation

HRID 1773544 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH3:9])=[C:4]([N+:10]([O-])=O)[CH:3]=1.O.C(=O)([O-])[O-].[K+].[K+]>C(OCC)(=O)C.N1C=CC=CC=1.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH3:9])=[C:4]([NH2:10])[CH:3]=1

Participants

6

Reactant 3

HCID 962WaterHCID 11430Potassium CarbonateHCID 15892659HCID 15892659, compound

Product 1

HCID 12465045HCID 12465045, compoundYield 104.9%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 66926435Pyridine waterSolvent

Procedure

To a solution of 4-chloro-1-ethyl-2-nitro-benzene (0.57 g, 3.08 mmol) in a mixture of ethyl acetate and ethanol (1/1, 30 mL) was added stannous chloride (1.7 g, 9.24 mmol) and the resulting mixture was stirred at room temperature overnight. The reaction mixture was then poured into water and basified by addition of potassium carbonate until pH>10. The resulting mixture was extracted with dichloromethane; the organic extracts were dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure. The crude residue was purified by flash chromatography to afford 0.503 g of 5-chloro-2-ethyl-phenylamine as a brown oil.

Workup

  1. extractionThe resulting mixture was extracted with dichloromethane
  2. dry with materialthe organic extracts were dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. customevaporated under reduced pressure
  5. customThe crude residue was purified by flash chromatography

Sources & evidence

ORD record
ord-9be3e575ada44cba868b43c1bdbc0bff
Source dataset
uspto-grants-2016_02
Patent number
US09255110B2

Reaction notes

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