Nitric Acid → HCID 10379608, compound

HRID 640797Notes

Reaction equation

HRID 640797 reaction equation
[C:1]([NH:4][C:5]1[C:6]([Cl:15])=[CH:7][C:8]([Cl:14])=[C:9]([CH:13]=1)[C:10]([OH:12])=[O:11])(=[O:3])[CH3:2].[N+:16]([O-])([OH:18])=[O:17]>S(=O)(=O)(O)O>[C:1]([NH:4][C:5]1[C:13]([N+:16]([O-:18])=[O:17])=[C:9]([C:8]([Cl:14])=[CH:7][C:6]=1[Cl:15])[C:10]([OH:12])=[O:11])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 944Nitric Acid2×HCID 2833165-(Acetylamino)-2,4-dichlorobenzoic acid

Product 1

HCID 10379608HCID 10379608, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Conditions

Temperature
0 °C

Procedure

5-Acetamido-2,4-dichlorobenzoic acid (9.6 g, 0.039 mol) was added in small portions over 30 min to a stirred ice-cooled solution of fuming nitric acid (1.8 mL, 0.043 mol) and conc sulfuric acid (120 mL). After the addition was complete, more fuming nitric acid (17 mL) and conc sulfuric acid (80 mL) were added at 30 min and 60 min intervals. The reaction mixture was then left to stir for an additional 2.5 h at 0° C., allowed to warm to 12-16° C. and left to stir at this temperature until all starting material was consumed (about 3 h). The solution was poured onto ice and extracted with ethyl acetate (3×). The organic extracts were combined, washed with brine, dried, and concentrated to give 3-acetamido-4,6-dichloro-2-nitrobenzoic acid as an orange solid (9.8 g, 86%).

Workup

  1. additionAfter the addition
  2. waitThe reaction mixture was then left
  3. temperatureto warm to 12-16° C.
  4. waitleft
  5. stirringto stir at this temperature until all starting material
  6. customwas consumed (about 3 h)
  7. additionThe solution was poured onto ice
  8. extractionextracted with ethyl acetate (3×)
  9. washwashed with brine
  10. customdried
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-c98c552c8ef945679f88f5ea803d7007
Source dataset
uspto-grants-2010_04
Patent number
US07692011B2

Reaction notes

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