Hydrochloric Acid → HCID 13065225, compound

HRID 66638Notes

Reaction equation

HRID 66638 reaction equation
[NH2:1][C:2]([CH2:22][F:23])([CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[C:8]([O:14]CC2C=CC=CC=2)[CH:7]=1)C#N.Cl.C1C=C2C(C(O)(O)C(=O)C2=CC=1)=[O:32].[CH3:38][OH:39]>>[NH2:1][C:2]([CH2:22][F:23])([CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[C:8]([OH:14])[CH:7]=1)[C:38]([OH:32])=[O:39]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 10236NinhydrinHCID 20487167HCID 20487167, compound

Product 1

HCID 13065225HCID 13065225, compound

Procedure

A solution of 2-amino-2-fluoromethyl-3-(3-benzyloxy-4-methoxyphenyl)propionitrile (0.7 g) in absolute methanol saturated with dry hydrogen chloride (50 ml) is heated at reflux for 12 hours. The methanol is evaporated and the residue dissolved in trifluoroacetic acid (10 ml). The mixture is heated at reflux temperature for 2 hours. Water (4 ml) is then added, and reflux continues overnight. The residue obtained upon evaporation under reduced pressure is passed through Amberlite 120 H+ ion exchange resin column. The ninhydrin positive fractions are pooled and concentrated. The residue is crystallized from water-methanol-ether to afford the desired product.

Workup

  1. temperatureat reflux for 12 hours
  2. customThe methanol is evaporated
  3. dissolutionthe residue dissolved in trifluoroacetic acid (10 ml)
  4. temperatureThe mixture is heated
  5. temperatureat reflux temperature for 2 hours
  6. additionWater (4 ml) is then added
  7. temperaturereflux
  8. customThe residue obtained upon evaporation under reduced pressure
  9. concentrationconcentrated
  10. customThe residue is crystallized from water-methanol-ether

Sources & evidence

ORD record
ord-cf5da4cd8dbe4f78a123d413e8504733
Source dataset
uspto-grants-1982_08
Patent number
US04342780

Reaction notes

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