Nitric Acid → HCID 10379608, compound

HRID 336426Notes

Reaction equation

HRID 336426 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].OS(O)(=O)=O.[N+:21]([O-])([OH:23])=[O:22]>>[C:1]([NH:4][C:5]1[C:13]([N+:21]([O-:23])=[O:22])=[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 3

HCID 944Nitric Acid3×HCID 1118Sulfuric Acid3×HCID 2833165-(Acetylamino)-2,4-dichlorobenzoic acid

Product 1

HCID 10379608HCID 10379608, compoundYield 81%

Procedure

5-Acetamido-2,4-dichlorobenzoic acid 1-4 (40.0 g, 0.161 mol) was added in portions to a cooled mixture of concentrated H2SO4 (400 mL) and concentrated nitric acid (400 mL) at 5° C. After stirring for 2 h concentrated H2SO4 (100 mL)/concentrated nitric acid (100 mL) was added. After another 90 min concentrated H2SO4 (400 mL)/concentrated nitric acid (200 mL) was added and stirring was continued for a further 2 h. The reaction mixture was cautiously poured onto ice resulting in the formation of a yellow precipitate. The product was collected by filtration then extracted into EtOAc. The combined organic layers were washed with H2O, brine, dried over Na2SO4, filtered and concentrated to provide the nitro compound 1-5 as a yellow/orange solid (38.1 g, 81% yield). 1H NMR (400 MHz, d6-DMSO) δ1.99 (s, 3H), 8.21 (s, 1H), 10.27 (s, 1H).

Workup

  1. additionwas added
  2. additionThe reaction mixture was cautiously poured onto ice resulting in the formation of a yellow precipitate
  3. filtrationThe product was collected by filtration
  4. extractionthen extracted into EtOAc
  5. washThe combined organic layers were washed with H2O, brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-5c1101a18edd4289aa3c3281b765e0c1
Source dataset
uspto-grants-2014_11
Patent number
US08889695B2

Reaction notes

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