Nitric Acid → 4-(4-Acetamido-3-nitrophenyl)pyridine

HRID 1730907Notes

Reaction equation

HRID 1730907 reaction equation
[N+:1]([O-:4])(O)=[O:2].[C:5]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=2)=[CH:11][CH:10]=1)(=[O:7])[CH3:6].[OH-].[Na+]>>[C:5]([NH:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]2[CH:16]=[CH:17][N:18]=[CH:19][CH:20]=2)=[CH:13][C:14]=1[N+:1]([O-:4])=[O:2])(=[O:7])[CH3:6]

Participants

4

Reactant 3

HCID 944Nitric AcidHCID 14798Sodium HydroxideHCID 205065194-(4-Acetamidophenyl)pyridine

Product 1

HCID 128507544-(4-Acetamido-3-nitrophenyl)pyridine

Procedure

To 160 ml. of nitric acid (90%) cooled to less than 0°C. in an ice-ethanol bath was slowly added with stirring 42 g. of 4-(4-acetamidophenyl)pyridine over a period of about twenty minutes. The reaction mixture was then stirred for 45 minutes, keeping the reaction temperature below 0°C. The reaction mixture was then poured onto ice and the mixture treated with 35% aqueous sodium hydroxide solution, adding ice to keep the mixture cool. The resulting yellow solid was collected, washed with water and air-dried to yield 43.7 g. of 4-(4-acetamido-3-nitrophenyl)pyridine, which was used directly in Example 4 without further purification.

Workup

  1. additionwas slowly added
  2. stirringThe reaction mixture was then stirred for 45 minutes
  3. customthe reaction temperature below 0°C
  4. additionThe reaction mixture was then poured onto ice
  5. additionadding ice
  6. temperaturecool
  7. customThe resulting yellow solid was collected
  8. washwashed with water
  9. customair-dried
  10. customto yield 43.7 g
  11. customof 4-(4-acetamido-3-nitrophenyl)pyridine, which was used directly in Example 4 without further purification

Sources & evidence

ORD record
ord-a46435569e8a48e5b57f11e2c39f118f
Source dataset
uspto-grants-1976_11
Patent number
US03994903

Reaction notes

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