Nitric Acid → 2'-Chloro-4'-fluoro-5'-nitroacetanilide

HRID 380796Notes

Reaction equation

HRID 380796 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]([F:12])[CH:9]=[CH:8][C:3]=1[NH:4][C:5](=[O:7])[CH3:6].[N+:13]([O-])([OH:15])=[O:14].O>S(=O)(=O)(O)O>[Cl:1][C:2]1[CH:11]=[C:10]([F:12])[C:9]([N+:13]([O-:15])=[O:14])=[CH:8][C:3]=1[NH:4][C:5](=[O:7])[CH3:6]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 962WaterHCID 5894192'-Chloro-4'-fluoroacetanilide

Product 1

HCID 183659292'-Chloro-4'-fluoro-5'-nitroacetanilide

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
6.5 °C

Procedure

A solution of 2′-chloro-4′-fluoroacetanilide (85.5 g, 456 mmol) in concentrated sulfuric acid is cooled to 0° C., treated slowly with 70% nitric acid (32 mL, 502 mmol) while maintaining the temperature from 5-8° C., stirred at room temperature overnight and poured into water. The resultant aqueous mixture is filtered to obtain a solid which is recrystallized from ethanol to give the title product as pale, yellow plates (27.0 g, mp 158-160° C.).

Workup

  1. filtrationThe resultant aqueous mixture is filtered
  2. customto obtain a solid which
  3. customis recrystallized from ethanol

Sources & evidence

ORD record
ord-19e7e5868f08421dbb7672ea8a0625ec
Source dataset
uspto-grants-2001_10
Patent number
US06303783B1

Reaction notes

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