Hydrochloric Acid → 4-Ethyl-3-nitroaniline

HRID 1773542Notes

Reaction equation

HRID 1773542 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([NH:9]C(=O)C)=[CH:5][C:4]=1[N+:13]([O-:15])=[O:14])[CH3:2].Cl.[OH-].[Na+]>>[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([NH2:9])=[CH:5][C:4]=1[N+:13]([O-:15])=[O:14])[CH3:2]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 22708659N-(4-ethyl-3-nitro-phenyl)-acetamide

Product 1

HCID 227086804-Ethyl-3-nitroanilineYield 75.3%

Procedure

A mixture of N-(4-ethyl-3-nitro-phenyl)-acetamide (1.0 g) and concentrated hydrochloric acid (5 mL) was heated at reflux for 4 hours. The reaction mixture was then cooled, basified by addition of sodium hydroxide and extracted twice with diethyl ether. The combined organic extracts were dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure to afford 0.601 g of 4-ethyl-3-nitro-phenylamine without further purifications. MS=167 [M+H]+.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 4 hours
  3. temperatureThe reaction mixture was then cooled
  4. extractionextracted twice with diethyl ether
  5. dry with materialThe combined organic extracts were dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-37b837b08be346059599d48d41648980
Source dataset
uspto-grants-2016_02
Patent number
US09255110B2

Reaction notes

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