Malonic Acid → 3-amino-3-(2,3-dihydro-1,4-benzodioxin-6-yl)propanoic acid

HRID 1371533Notes

Reaction equation

HRID 1371533 reaction equation
[O:1]1[C:6]2[CH:7]=[CH:8][C:9]([CH:11]=O)=[CH:10][C:5]=2[O:4][CH2:3][CH2:2]1.[C:13]([OH:19])(=[O:18])[CH2:14]C(O)=O.C([O-])(=O)C.[NH4+:24]>CCO>[NH2:24][CH:11]([C:9]1[CH:8]=[CH:7][C:6]2[O:1][CH2:2][CH2:3][O:4][C:5]=2[CH:10]=1)[CH2:14][C:13]([OH:19])=[O:18]

Participants

5

Reactant 3

HCID 867Malonic AcidHCID 2481272,3-Dihydro-1,4-benzodioxin-6-carbaldehydeHCID 517165Ammonium Acetate

Product 1

HCID 35364503-amino-3-(2,3-dihydro-1,4-benzodioxin-6-yl)propanoic acidYield 28.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 5 g of 2,3-dihydrobenzo[1,4]dioxine-6-carbaldehyde, 3.17 g of malonic acid and 4.69 g of ammonium acetate in 50 ml of EtOH is refluxed for 5 hours. The reaction mixture is allowed to cool to RT and the precipitate formed is filtered off by suction and washed with EtOH and then with water. 1.965 g of the expected product are obtained after drying under vacuum.

Workup

  1. temperatureis refluxed for 5 hours
  2. customthe precipitate formed
  3. filtrationis filtered off by suction
  4. washwashed with EtOH

Sources & evidence

ORD record
ord-24aa4dc4f9044169ba58e0a9c056c3b4
Source dataset
uspto-grants-2007_01
Patent number
US07157454B2

Reaction notes

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