Malonic Acid → 3-amino-3-(3-iodophenyl)propanoic acid

HRID 557464Notes

Reaction equation

HRID 557464 reaction equation
[C:1](O)(=O)[CH2:2][C:3]([OH:5])=[O:4].[I:8][C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][CH:16]=1)C=O.C([O-])(=O)C.[NH4+:21]>C(O)C>[NH2:21][CH:1]([C:15]1[CH:14]=[CH:11][CH:10]=[C:9]([I:8])[CH:16]=1)[CH2:2][C:3]([OH:5])=[O:4]

Participants

5

Reactant 3

HCID 867Malonic AcidHCID 2526103-IodobenzaldehydeHCID 517165Ammonium Acetate

Product 1

HCID 27723423-amino-3-(3-iodophenyl)propanoic acidYield 54%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Malonic acid (2.2 g, 21.5 mmol) and 3-iodobenzaldehyde (5 g, 21.5 mmol) were suspended in ethanol (50 mL) and ammonium acetate (1.66 g, 21.5 mmol) was added and the reaction heated to a reflux overnight. The reaction was cooled to room temperature filtered and washed with ethanol followed by ether and dried to afford the product (3.4 g, 11.6 mmol, 54%) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ 7.80 (s, 1H), 7.64 (dd, J=7.8 Hz, 1H), 7.42 (dd, J=7.6 Hz, 1H), 7.16 (dd, J=7.8 Hz, 1H), 7.14 (dd, J=7.6 Hz, 1H), 4.21 (m, 1H), 2.36 (m, 2H).

Workup

  1. temperaturethe reaction heated to a reflux overnight
  2. filtrationfiltered
  3. washwashed with ethanol
  4. customdried

Sources & evidence

ORD record
ord-b85aaa88beb84716a7adfd6721e24bee
Source dataset
uspto-grants-2011_11
Patent number
US08058449B2

Reaction notes

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