Ammonia → Methoxymalonamic acid

HRID 129073Notes

Reaction equation

HRID 129073 reaction equation
[CH3:1][O:2][CH:3]([C:8]([O-:10])=O)[C:4]([O:6]C)=[O:5].[NH3:11]>C(Cl)Cl>[CH3:1][O:2][CH:3]([C:8]([NH2:11])=[O:10])[C:4]([OH:6])=[O:5]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 229990802,3-Dimethoxy-3-oxopropanoate

Product 1

HCID 19373134Methoxymalonamic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 10.4 g of monomethyl methoxymalonate in 70 ml of methylene chloride was added dropwise at -10° C. to 26 ml of 25 percent aqueous ammonia. After stirring the mixture was evaporated and the residue was dissolved in water and chromatographed on a cation exchanger with water. The eluate was concentrated and the residue was triturated with diethyl ether and filtered off. The precipitate was washed with water and dried. There were obtained 8.9 g of methoxymalonamic acid, m.p. 128°-130° C.

Workup

  1. customwas evaporated
  2. dissolutionthe residue was dissolved in water
  3. customchromatographed on a cation exchanger with water
  4. concentrationThe eluate was concentrated
  5. customthe residue was triturated with diethyl ether
  6. filtrationfiltered off
  7. washThe precipitate was washed with water
  8. customdried

Sources & evidence

ORD record
ord-ba2ee0b710fe47d69c878baff79ad264
Source dataset
uspto-grants-1995_11
Patent number
US05466708

Reaction notes

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