Malonate Ion → 3-Amino-3-(3-methylthiophen-2-yl)propanoic acid

HRID 1258799Notes

Reaction equation

HRID 1258799 reaction equation
[CH3:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[CH:7]=O.[C:9]([O-:12])(=[O:11])[CH3:10].[NH4+:13].C([O-])(=O)CC([O-])=O>>[NH2:13][CH:7]([C:3]1[S:4][CH:5]=[CH:6][C:2]=1[CH3:1])[CH2:10][C:9]([OH:12])=[O:11]

Participants

4

Reactant 3

HCID 9084Malonate IonHCID 799113-Methyl-2-thiophenecarboxaldehydeHCID 517165Ammonium Acetate

Product 1

HCID 247011743-Amino-3-(3-methylthiophen-2-yl)propanoic acid

Procedure

12.6 g of 3-methyl-thiophene-2-carbaldehyde was dissolved in 150 mL of 95% alcohol, and 15.4 g of ammonium acetate was added at 45° C., then 20.8 g of malonate was added. The solution was refluxed for 16 hours, then cooled, and filtered to give a solid of 3-amino-3-(3-methyl-thiophene-2-yl)propionic acid.

Workup

  1. temperatureThe solution was refluxed for 16 hours
  2. temperaturecooled
  3. filtrationfiltered

Sources & evidence

ORD record
ord-af6eacd5e9b2428db362efc1dd49f725
Source dataset
uspto-grants-2013_06
Patent number
US08466191B2

Reaction notes

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