Hydrochloric Acid → HCID 15892659, compound

HRID 924664Notes

Reaction equation

HRID 924664 reaction equation
N([O-])=O.[Na+].O.[CH2:6]([C:8]1[CH:14]=[CH:13][C:11](N)=[CH:10][C:9]=1[N+:15]([O-:17])=[O:16])[CH3:7].[ClH:18]>[Cu]Cl>[Cl:18][C:11]1[CH:13]=[CH:14][C:8]([CH2:6][CH3:7])=[C:9]([N+:15]([O-:17])=[O:16])[CH:10]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 227086804-Ethyl-3-nitroanilineHCID 23668193Sodium Nitrite

Product 1

HCID 15892659HCID 15892659, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 62652Cuprous chlorideCatalyst

Procedure

A solution of sodium nitrite in water (4.2 g, 60 mmol, 5 M, 12 mL) was added drop wise to a cooled (0° C.) solution of 4-ethyl-3-nitroaniline (10 g, 60 mmol) in conc. HCl (200 mL) and the reaction mixture was stirred at the same temperature for 1.5 h. Copper (I) chloride (9.5 g, 96 mmol) was then added and the solution was stirred at room temperature for 1 h and then at 80° C. for an additional hour. After cooling down the reaction mixture was extracted with DCM (3×100 mL) and the combined organic layers were dried over sodium sulfate. The crude was then purified by flash chromatography (hexane/EtOAc 9/1) to obtain the title compound as a yellow oil (6.28 g, 56%).

Workup

  1. stirringthe solution was stirred at room temperature for 1 h
  2. waitat 80° C. for an additional hour
  3. temperatureAfter cooling down the reaction mixture
  4. extractionwas extracted with DCM (3×100 mL)
  5. dry with materialthe combined organic layers were dried over sodium sulfate
  6. customThe crude was then purified by flash chromatography (hexane/EtOAc 9/1)

Sources & evidence

ORD record
ord-e6d66f6e9a7847f0bacfc7e3c840e78a
Source dataset
uspto-grants-2016_03
Patent number
US09283224B2

Reaction notes

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