Potassium Nitrate → N-(4-Chloro-5-cyano-2-nitro-phenyl)-acetamide

HRID 538117Notes

Reaction equation

HRID 538117 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:11])[CH3:10])=[CH:4][C:3]=1[C:12]#[N:13].[N+:14]([O-])([O-:16])=[O:15].[K+]>S(=O)(=O)(O)O>[Cl:1][C:2]1[C:3]([C:12]#[N:13])=[CH:4][C:5]([NH:8][C:9](=[O:11])[CH3:10])=[C:6]([N+:14]([O-:16])=[O:15])[CH:7]=1

Participants

4

Reactant 2

HCID 24434Potassium NitrateHCID 25638344N-(4-Chloro-3-cyanophenyl)acetamide

Product 1

HCID 66937079N-(4-Chloro-5-cyano-2-nitro-phenyl)-acetamideYield 29%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Conditions

Temperature
0 °C

Procedure

N-(4-Chloro-3-cyano-phenyl)-acetamide (3.00 g, 15.4 mmol) was dissolved in conc. sulfuric acid (15 mL) and cooled to 0° C. A solution of potassium nitrate (3.12 g, 30.8 mmol) in conc. sulfuric acid (15 mL) was added drop-wise with stirring. The reaction mixture was kept at 0° C. for 3.5 h, then slowly added to stirred ice/water. The resulting precipitate was collected, dissolved in EtOAc, dried, filtered, and concentrated. The residue was purified (FCC) (10-80% EtOAc/hexanes) to yield the titled compound (1.06 g, 29% yield). This compound did not yield MS data. 1H NMR (400 MHz, CDCl3): 10.60 (s, 1H), 9.18 (s, 1H), 8.58 (s, 1H), 2.36 (s, 3H).

Workup

  1. additionslowly added
  2. customThe resulting precipitate was collected
  3. dissolutiondissolved in EtOAc
  4. customdried
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified (FCC) (10-80% EtOAc/hexanes)

Sources & evidence

ORD record
ord-66f81fddcd90426db8f68d913ff2055f
Source dataset
uspto-grants-2014_10
Patent number
US08865713B2

Reaction notes

Loading…