Malonic Acid → (RS)-beta-Amino-beta-(4-bromophenyl)propionic acid

HRID 658138Notes

Reaction equation

HRID 658138 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][CH:3]=1.[C:10]([OH:16])(=[O:15])[CH2:11]C(O)=O.C([O-])(=O)C.[NH4+:21]>C(O)C>[NH2:21][CH:6]([C:5]1[CH:8]=[CH:9][C:2]([Br:1])=[CH:3][CH:4]=1)[CH2:11][C:10]([OH:16])=[O:15]

Participants

5

Reactant 3

HCID 867Malonic AcidHCID 707414-BromobenzaldehydeHCID 517165Ammonium Acetate

Product 1

HCID 554034(RS)-beta-Amino-beta-(4-bromophenyl)propionic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-Bromobenzaldehyde (50.0 g, 270 mmol), malonic acid (28.1 g, 270 mmol) and ammonium acetate (27.7 g, 359 mmol, 1.3 eq.) are dissolved in ethanol (400 ml). The mixture is heated at reflux for 16 h. The resulting solid is collected on a glass filter funnel, collected with suction filtration and washed with ethanol. The residue is then recrystallized from methanol (80 ml). It is subsequently triturated with ethyl acetate and collected by suction filtration. 41.0 g (0.16 mmol, 62% of theory) of the title compound are obtained as a colorless crystalline solid.

Workup

  1. temperatureThe mixture is heated
  2. temperatureat reflux for 16 h
  3. customThe resulting solid is collected on a glass
  4. filtrationfilter funnel
  5. filtrationcollected with suction filtration
  6. washwashed with ethanol
  7. customThe residue is then recrystallized from methanol (80 ml)
  8. customIt is subsequently triturated with ethyl acetate
  9. filtrationcollected by suction filtration

Sources & evidence

ORD record
ord-d33f66fa40774fc9b180b6abb8e9e78a
Source dataset
uspto-grants-2011_12
Patent number
US08076285B2

Reaction notes

Loading…