Malonic Acid → 3-Amino-5-methylhexanoic acid

HRID 326766Notes

Reaction equation

HRID 326766 reaction equation
[CH:1](=O)[CH2:2][CH:3]([CH3:5])[CH3:4].[C:7]([OH:13])(=[O:12])[CH2:8]C(O)=O.C([O-])(=O)C.[NH4+:18]>C(O)C>[NH2:18][CH:1]([CH2:2][CH:3]([CH3:5])[CH3:4])[CH2:8][C:7]([OH:13])=[O:12]

Participants

5

Reactant 3

HCID 867Malonic AcidHCID 115523-MethylbutanalHCID 517165Ammonium Acetate

Product 1

HCID 27337353-Amino-5-methylhexanoic acidYield 55.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 43.06 gm (500 mMol) isovaleraldehyde in ethanol (150 ml) were added 52 gm (500 mMol) malonic acid followed by 57.75 gm (750 mMol) ammonium acetate. The suspension was stirred at reflux for 5 hours and the resulting solution was then cooled to 0° C. The resulting solid was filtered, washed with 1:1 ethyl acetate:ethanol (200 ml) and dried under vacuum for 18 hours to give 40 gm of crude 3-amino-5-methylhexanoic acid.

Workup

  1. temperatureat reflux for 5 hours
  2. filtrationThe resulting solid was filtered
  3. washwashed with 1:1 ethyl acetate
  4. dry with materialethanol (200 ml) and dried under vacuum for 18 hours

Sources & evidence

ORD record
ord-d4f7f956968f44079406927e5f81b4dc
Source dataset
uspto-grants-1993_12
Patent number
US05270328

Reaction notes

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