Hydrochloric Acid → 2-Amino-2-(thiophen-3-yl)acetic acid

HRID 372110Notes

Reaction equation

HRID 372110 reaction equation
[N:1]([CH:4]([C:8]1[CH:12]=[CH:11][S:10][CH:9]=1)[C:5]([OH:7])=[O:6])=[N+]=[N-].Cl>[Pd].C(O)C>[NH2:1][CH:4]([C:8]1[CH:12]=[CH:11][S:10][CH:9]=1)[C:5]([OH:7])=[O:6]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 20312080HCID 20312080, compound

Product 1

HCID 1025772-Amino-2-(thiophen-3-yl)acetic acid

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

0.3 g. of palladium/barium sulfate catalyst are added to a solution of 6 g. of DL-α-azido-3-thiopheneacetic acid in 40 ml. of ethanol and 40 ml. of 0.5N hydrochloric acid. Hydrogenation takes place at about 60 psig. after 2 hours. After filtration, the volume is concentrated to about 30 ml. When the pH is brought to 6.5 with ammonia, the amino acid separates as a white powder. After washing with ethanol/water and drying, 3.5 g. of the product, DL-α-amino-3-thiopheneacetic acid, are obtained; m.p. 283°-285°.

Workup

  1. filtrationAfter filtration
  2. concentrationthe volume is concentrated to about 30 ml
  3. washAfter washing with ethanol/water
  4. customdrying

Sources & evidence

ORD record
ord-a9acfbd5e9234ba7be62368f93c3254a
Source dataset
uspto-grants-1978_05
Patent number
US04088816

Reaction notes

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