Potassium Cyanide → HCID 54032708, compound

HRID 1679929Notes

Reaction equation

HRID 1679929 reaction equation
N([O-])=O.[Na+].N[C:6]1[CH:19]=[CH:18][C:9]([C:10]([C@H:12]2[CH2:14][C@H:13]2[C:15]([OH:17])=[O:16])=[O:11])=[CH:8][CH:7]=1.C(=O)([O-])[O-].[Na+].[Na+].[Cu][C:27]#[N:28].[C-]#N.[K+]>O.Cl.C1(C)C=CC=CC=1>[C:27]([C:6]1[CH:19]=[CH:18][C:9]([C:10]([C@H:12]2[CH2:14][C@H:13]2[C:15]([OH:17])=[O:16])=[O:11])=[CH:8][CH:7]=1)#[N:28]

Participants

9

Reactant 5

HCID 9032Potassium CyanideHCID 10340Sodium CarbonateHCID 23668193Sodium NitriteHCID 54423379HCID 54423379, compoundHCID 178418546HCID 178418546, compound

Product 1

HCID 54032708HCID 54032708, compoundYield 33.4%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent3×HCID 1140TolueneSolvent

Conditions

Temperature
0 °C

Procedure

A cold solution of 3.4 g (49.3 millimoles) of sodium nitrite in 25 ml of water is added to a solution of 10.0 g (48.7 millimoles) of cis-2-(p-aminobenzoyl)-cyclopropanecarboxylic acid (see Example 9a) in 37 ml of concentrated hydrochloric acid and 190 ml of water, whilst stirring at 0° C. The mixture is then stirred for a further 10 minutes, at 0°-5° C., after which it is neutralized with sodium carbonate at the same temperature. The solution obtained is added dropwise, whilst stirring, to a cold (0°-5° C.) solution of 5.3 g (59.2 millimoles) of copper-(I) cyanide and 7.5 g (115.2 millimoles) of potassium cyanide in 150 ml of water, which is covered with a layer of 40 ml of toluene. The mixture is then stirred for 30 minutes at 5° C., followed by 12 hours at room temperature. It is filtered and the filtrate is acidified with concentrated hydrochloric acid. The solid which precipitates is filtered off, washed with water and extracted with hot ethanol. Concentrating the ethanol extract gives 3.5 g (33% of theory) of cis-2-(p-cyanobenzoyl)-cyclopropanecarboxylic acid as pale brown crystals, of melting point 180°-182° C.

Workup

  1. stirringThe mixture is then stirred for a further 10 minutes, at 0°-5° C.
  2. customThe solution obtained
  3. additionis added dropwise
  4. stirringThe mixture is then stirred for 30 minutes at 5° C.
  5. filtrationIt is filtered
  6. customThe solid which precipitates
  7. filtrationis filtered off
  8. washwashed with water
  9. extractionextracted with hot ethanol
  10. concentrationConcentrating the ethanol
  11. extractionextract

Sources & evidence

ORD record
ord-e0c0e7a9700a4b00b09c410a55659e32
Source dataset
uspto-grants-1981_06
Patent number
US04271163

Reaction notes

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