Potassium Cyanide → 2-Amino-2-(4-carboxy-2-phenylphenyl)acetic acid

HRID 343940Notes

Reaction equation

HRID 343940 reaction equation
C(C1[CH:10]=[CH:9][C:6]([CH:7]=O)=[C:5]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:4]=1)#N.[C:17](=[O:20])([O-:19])[O-].[NH4+:21].[NH4+].[C-]#N.[K+].[CH2:26]([OH:28])[CH3:27].[OH2:29]>O>[NH2:21][CH:7]([C:6]1[CH:9]=[CH:10][C:27]([C:26]([OH:29])=[O:28])=[CH:4][C:5]=1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:17]([OH:19])=[O:20]

Participants

6

Reactant 4

HCID 9032Potassium CyanideHCID 517111Ammonium CarbonateHCID 19096565Water ethanolHCID 54551655HCID 54551655, compound

Product 1

HCID 540294072-Amino-2-(4-carboxy-2-phenylphenyl)acetic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
85 °C

Procedure

A stirred mixture of 4-cyano-2-phenylbenzaldehyde (0.15 g, 0.7 mmol), ammonium carbonate (0.27 g, 2.8 mmol) and potassium cyanide (91 mg, 1.4 mmol) in ethanol-water (1:1, 4 ml) was heated to 85° C. for 4 hours in a sealed vessel. After cooling, the mixture was diluted with water (2 ml) and cautiously acidified to pH1 precipitating a sticky solid. The crude solid was dissolved in 2M sodium hydroxide and heated to 120° C. for 16 hours in a sealed vessel. After cooling, the reaction solution was chromatographed directly on ion exchange resin, as described in Example 3 (iii) to give the title product as a white solid, m.p. 238°-240° C.

Workup

  1. temperatureAfter cooling
  2. customprecipitating a sticky solid
  3. dissolutionThe crude solid was dissolved in 2M sodium hydroxide
  4. temperatureheated to 120° C. for 16 hours in a sealed vessel
  5. temperatureAfter cooling
  6. customthe reaction solution was chromatographed directly on ion exchange resin

Sources & evidence

ORD record
ord-afa81b9866f1462da0d6efedfe461099
Source dataset
uspto-grants-1999_01
Patent number
US05863947

Reaction notes

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