Potassium Nitrate → HCID 86701550, compound

HRID 2173983Notes

Reaction equation

HRID 2173983 reaction equation
[C:1]([C:3]1[C:4]([CH3:13])=[C:5]([NH:9][C:10](=[O:12])[CH3:11])[CH:6]=[CH:7][CH:8]=1)#[N:2].[N+:14]([O-])([O-:16])=[O:15].[K+]>S(=O)(=O)(O)O>[C:1]([C:3]1[C:4]([CH3:13])=[C:5]([NH:9][C:10](=[O:12])[CH3:11])[C:6]([N+:14]([O-:16])=[O:15])=[CH:7][CH:8]=1)#[N:2]

Participants

4

Reactant 2

HCID 24434Potassium NitrateHCID 20462515HCID 20462515, compound

Product 1

HCID 86701550HCID 86701550, compound

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Conditions

Temperature
-10 °C

Procedure

To a solution of N-(3-cyano-2-methylphenyl)acetamide (CAS #: 70946-79-1) (1.8 g, 10.33 mmol) in conc. sulfuric acid (20 mL) at −10° C., potassium nitrate (2.08 g, 20.67 mmol) in 5 mL of conc. sulfuric acid was added slowly. After addition, the reaction was stirred at −10° C. for 30 min, then at 0° C. for 3.5 hr. The reaction mixture was poured onto ice, and then the precipitate was collected by filtration. The solid was washed with water and then purified by silica gel flash column chromatography (heptanes/EtOAc=1/0 to 1/1) to give the title compound. MS (ESI−) m/z 218.0 (M−H).

Workup

  1. additionAfter addition
  2. waitat 0° C. for 3.5 hr
  3. additionThe reaction mixture was poured onto ice
  4. filtrationthe precipitate was collected by filtration
  5. washThe solid was washed with water
  6. custompurified by silica gel flash column chromatography (heptanes/EtOAc=1/0 to 1/1)

Sources & evidence

ORD record
ord-b12ef864034142028b5fd58a6995bb84
Source dataset
uspto-grants-2015_06
Patent number
US09056874B2

Reaction notes

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