Malonic Acid → 3-Amino-3-(3-bromophenyl)propanoic acid

HRID 501694Notes

Reaction equation

HRID 501694 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=O.[C:10]([OH:16])(=[O:15])[CH2:11]C(O)=O.C([O-])(=O)C.[NH4+:21]>C(O)C>[NH2:21][CH:5]([C:4]1[CH:7]=[CH:8][CH:9]=[C:2]([Br:1])[CH:3]=1)[CH2:11][C:10]([OH:16])=[O:15]

Participants

5

Reactant 3

HCID 867Malonic AcidHCID 765833-BromobenzaldehydeHCID 517165Ammonium Acetate

Product 1

HCID 6036193-Amino-3-(3-bromophenyl)propanoic acidYield 70%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

Step Z (1). A mixture of 200 grams (1.08 mol) of 3-bromobenzaldehyde, 112 grams (1.08 mol) of malonic acid, and 166.5 g (2.16 mol) of ammonium acetate was suspended in 1.125 liters of absolute ethanol. The mixture was mechanically stirred and brought to reflux temperature, whereupon the solution clarified. The mixture was kept at reflux for 16 h, and a precipitate formed. The mixture was chilled to 0° C., and the solid product was collected by filtration and washed with cold ethanol to yield 184 grams (70%) of 3-amino-3-(3-bromophenyl)propanoic acid as a white solid which was carried forward without further purification or analytical characterization.

Workup

  1. temperatureto reflux temperature
  2. temperatureat reflux for 16 h
  3. customa precipitate formed
  4. filtrationthe solid product was collected by filtration
  5. washwashed with cold ethanol

Sources & evidence

ORD record
ord-84534cc5f30a4e89919fc92117e64f17
Source dataset
uspto-grants-2010_08
Patent number
US07772221B2

Reaction notes

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