Hydrochloric Acid → 4-Amino-3-fluorobenzenepropanoic acid

HRID 1389112Notes

Reaction equation

HRID 1389112 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][C:12]=1[N+:13]([O-])=O)[CH:5]=[CH:6][C:7]([OH:9])=[O:8].Cl.[H][H]>C(O)C.[Pd]>[F:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][C:12]=1[NH2:13])[CH2:5][CH2:6][C:7]([OH:9])=[O:8]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 542673383-(3-Fluoro-4-nitrophenyl)-2-propenoic acidHCID 178418361HCID 178418361, compound

Product 1

HCID 205364634-Amino-3-fluorobenzenepropanoic acid

Reagents, catalysts & solvents 2

HCID 702EthanolCatalystHCID 23938PalladiumCatalyst

Procedure

A mixture of 5.0 g. of 3-fluoro-4-nitrocinnamic acid and 100 mg. of 10% palladium-on-carbon in 200 ml. of ethanol containing 5 drops of 5.5 N ethanolic hydrogen chloride is treated with hydrogen in a Parr apparatus at room temperature for 3 hours. The mixture is then filtered through Celite and the filtrate is concentrated, affording 3-fluoro-4-aminohydrocinnamic acid.

Workup

  1. additionA mixture of 5.0 g
  2. filtrationThe mixture is then filtered through Celite
  3. concentrationthe filtrate is concentrated

Sources & evidence

ORD record
ord-fbc5edd3bbd446debaf8715dd50c9ad6
Source dataset
uspto-grants-1981_01
Patent number
US04243609

Reaction notes

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