Nitric Acid → 2-chloro-N-(3-fluoro-2-methyl-6-nitrophenyl)acetamide

HRID 2233163Notes

Reaction equation

HRID 2233163 reaction equation
[Cl:1][CH2:2][C:3]([NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([F:12])[C:7]=1[CH3:13])=[O:4].C(O)C.O.C(=O)=O.[N+:21]([O-])([OH:23])=[O:22]>S(=O)(=O)(O)O>[Cl:1][CH2:2][C:3]([NH:5][C:6]1[C:11]([N+:21]([O-:23])=[O:22])=[CH:10][CH:9]=[C:8]([F:12])[C:7]=1[CH3:13])=[O:4]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 9542492-chloro-N-(3-fluoro-2-methylphenyl)acetamideHCID 86603989Ethanol water dry ice

Product 1

HCID 675482572-chloro-N-(3-fluoro-2-methyl-6-nitrophenyl)acetamideYield 95%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

A solution of 2-chloro-N-(3-fluoro-2-methylphenyl)acetamide (47.2 g, 234 mmol) in conc. sulphuric acid (220 ml) was treated at ca. −20° C. (ethanol/water/CO2(s) bath) with conc. nitric acid (69%, 15.25 ml, 19 g, 235 mmol) over 30 minutes, keeping internal temperature ≦9° C. The reaction was complete at the end of the addition. The mixture was added to ice with vigorous stirring then left to stand overnight. Filtration, washing of the solid with water and drying afforded the product (54.6 g, 95%) containing ˜9% impurity.

Workup

  1. customtemperature ≦9° C
  2. additionThe reaction was complete at the end of the addition
  3. additionThe mixture was added to ice
  4. waitthen left
  5. filtrationFiltration
  6. washwashing of the solid with water
  7. customdrying

Sources & evidence

ORD record
ord-4f94485573634b06b3eb957d2b77e486
Source dataset
uspto-grants-2010_05
Patent number
US07709483B2

Reaction notes

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