Potassium Cyanide → Methyl 2-chloro-4-cyanobenzoate

HRID 1873929Notes

Reaction equation

HRID 1873929 reaction equation
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7](N)=[CH:6][C:5]=1[Cl:11].N([O-])=O.[Na+].N(O)=O.C([O-])(O)=O.[Na+].[C:25]([Cu])#[N:26].[C-]#N.[K+]>OS(O)(=O)=O.O>[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([C:25]#[N:26])=[CH:6][C:5]=1[Cl:11]

Participants

9

Reactant 6

HCID 9032Potassium CyanideHCID 24529Nitrous AcidHCID 516892Sodium BicarbonateHCID 11839197Methyl 4-Amino-2-chlorobenzoateHCID 23668193Sodium NitriteHCID 178418546HCID 178418546, compound

Product 1

HCID 53845357Methyl 2-chloro-4-cyanobenzoate

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
0 °C

Procedure

4-Amino-2-chloro-benzoic acid methyl ester (25 g, 72.7 mmol) was dissolved in 10% aqueous H2SO4 (150 mL) and the solution was cooled to 0° C. A solution of NaNO2 (11.15 g, 16.88 mmol) in water (50 mL) was added dropwise maintaining the temperature between 0-5° C. The mixture was stirred for 10 min., excess nitrous acid was neutralized using a saturated aqueous NaHCO3 solution. The resulting mixture was then added to a precooled (0-5° C.) suspension of CuCN (13.87 g, 155 mmol) and KCN (10.07 g, 155 mmol) in water (200 mL). It was stirred for 10 min., then allowed to attain room temperature. It was stirred for 0.5 h and finally heated on a steam bath for 0.5 h. Excess saturated FeCl3 solution was then added to the reaction mixture.

Workup

  1. temperaturemaintaining the temperature between 0-5° C
  2. stirringIt was stirred for 10 min.
  3. customto attain room temperature
  4. stirringIt was stirred for 0.5 h
  5. temperaturefinally heated on a steam bath for 0.5 h

Sources & evidence

ORD record
ord-a6d4ef0d67154d99ae579a84b567b2dd
Source dataset
uspto-grants-2012_11
Patent number
US08304449B2

Reaction notes

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