Hydrochloric Acid → α-Amino-3-fluorobenzeneacetic acid

HRID 322698Notes

Reaction equation

HRID 322698 reaction equation
[C-]#N.[K+].[C:4](=[O:7])([O-])[O-:5].[NH4+].[NH4+].[F:10][C:11]1[CH:12]=[C:13]([CH:16]=[CH:17][CH:18]=1)[CH:14]=O.Cl.[NH:20]1CC(=O)NC1=O.[OH-].[Na+]>O.CCO>[NH2:20][CH:14]([C:13]1[CH:16]=[CH:17][CH:18]=[C:11]([F:10])[CH:12]=1)[C:4]([OH:5])=[O:7]

Participants

9

Reactant 6

HCID 313Hydrochloric AcidHCID 9032Potassium CyanideHCID 10006HydantoinHCID 14798Sodium HydroxideHCID 680093-FluorobenzaldehydeHCID 517111Ammonium Carbonate

Product 1

HCID 265434α-Amino-3-fluorobenzeneacetic acid

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
23 °C

Procedure

Potassium cyanide (6.3, 0.1 mol) and ammonium carbonate (15.7 g, 0.2 mol) were dissolved in 50 mL of water (in a well ventilated fume hood). 3-Fluorobenzaldehyde (5.0 g, 0.04 mol) was dissolved in 50 mL of EtOH and added to the reaction. After stirring at reflux under nitrogen atmosphere for 17 hours, the reaction was cooled to 23° C., the pH adjusted to 2.0 by the addition of 5 N HCl and cooled to 5° C. The resulting hydantoin was collected, rinsed with cold water and vacuum dried giving 3.59 of an off-white solid. The hydantoin was hydrolyzed at reflux using 1 N NaOH giving 2-amino-2-(3-fluorophenyl)acetic acid which was esterified via Procedure H in methanol to give the title compound.

Workup

  1. additionadded to the reaction
  2. temperatureat reflux under nitrogen atmosphere for 17 hours
  3. temperaturecooled to 5° C
  4. customThe resulting hydantoin was collected
  5. washrinsed with cold water and vacuum
  6. customdried
  7. customgiving 3.59 of an off-white solid
  8. temperatureat reflux

Sources & evidence

ORD record
ord-d8bb4ac32b544f328e3cfe27be3f4489
Source dataset
uspto-grants-2001_04
Patent number
US06211235B1

Reaction notes

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