Hydrochloric Acid → 2-Nitroaniline

HRID 2259249Notes

Reaction equation

HRID 2259249 reaction equation
[N+:1]([C:4]1[CH:13]=[CH:12][CH:11]=[CH:10][C:5]=1[NH:6]C(=O)C)([O-:3])=[O:2].Cl>CO>[N+:1]([C:4]1[CH:13]=[CH:12][CH:11]=[CH:10][C:5]=1[NH2:6])([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 11090Acetamide, N-(2-nitrophenyl)-

Product 1

HCID 69462-NitroanilineYield 108.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 1.32 g of an o-nitroacetoanilide compound having the formula (XXV), ##STR23## 5 ml of conc. hydrochloric acid and 50 ml of methanol was heated under reflux for 80 minutes. The reaction solution was concentrated, poured into ice water and alkalified with potassium carbonate. After extraction with ethyl acetate, the organic layer was washed with water and dried over anhydrous sodium sulfate. Removing the solvent from the dried layer by distillation gave 1.1 g of an o-nitroaniline compound [compound (306)] having the formula (XXIV).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 80 minutes
  3. concentrationThe reaction solution was concentrated
  4. additionpoured into ice water
  5. extractionAfter extraction with ethyl acetate
  6. washthe organic layer was washed with water
  7. dry with materialdried over anhydrous sodium sulfate
  8. customRemoving the solvent from the dried layer
  9. distillationby distillation

Sources & evidence

ORD record
ord-fb32f14c4c7f40fea80f8e2eef6858c4
Source dataset
uspto-grants-1995_12
Patent number
US05472974

Reaction notes

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