Nitric Acid → n-(2,3-Dichloro-6-nitrophenyl)acetamide

HRID 463615

Reaction equation

HRID 463615 reaction equation
[CH3:1][C:2]([NH:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([Cl:11])[C:6]=1[Cl:12])=[O:3].[N+:13]([O-])([OH:15])=[O:14]>>[CH3:1][C:2]([NH:4][C:5]1[C:10]([N+:13]([O-:15])=[O:14])=[CH:9][CH:8]=[C:7]([Cl:11])[C:6]=1[Cl:12])=[O:3]

Participants

3

Reactant 2

HCID 944Nitric AcidHCID 247148N-(2,3-dichlorophenyl)acetamide

Product 1

HCID 291466n-(2,3-Dichloro-6-nitrophenyl)acetamide

Procedure

Nitric acid (30 ml) is cooled to -5°, and N-methylcarbonyl 2,3-dichloroaniline (9.8 g, 48 mmol) is added to the acid in small portions, with the temperature maintained at -5° or lower. After the addition is complete, the reaction is stirred for 1 hour at +5°. The reaction is then added dropwise to about 150 g of ice-water mixture. The resulting solid is collected by filtration and purified by prep. TLC (developing with 30% ethyl acetate/hexane). The least polar component is isolated to give N-methylcarbonyl 2,3-dichloro-6-nitroaniline.

Workup

  1. temperaturemaintained at -5°
  2. additionAfter the addition
  3. filtrationThe resulting solid is collected by filtration
  4. custompurified by prep
  5. customThe least polar component is isolated

Sources & evidence

ORD record
ord-a161289efb534d679a20b921d5c5cdd2
Source dataset
uspto-grants-1985_10
Patent number
US04544400

Linked notes

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