Hydrochloric Acid → Methyl 3-amino-2-(ethoxyimino)-3-oxopropanoate

HRID 1247917Notes

Reaction equation

HRID 1247917 reaction equation
[CH2:1]([O:3][N:4]=[C:5]([C:10]([O:12][CH3:13])=[O:11])[C:6](OC)=[O:7])[CH3:2].[OH-].[NH4+:15].Cl>CO>[C:6]([C:5](=[N:4][O:3][CH2:1][CH3:2])[C:10]([O:12][CH3:13])=[O:11])(=[O:7])[NH2:15]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14923Ammonium HydroxideHCID 582108Propanedioic acid, (ethoxyimino)-, dimethyl ester

Product 1

HCID 53690437Methyl 3-amino-2-(ethoxyimino)-3-oxopropanoate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of dimethyl ethoxyiminomalonate (57.4 g) and conc. ammonium hydroxide (50 ml) in methanol (150 ml) was stirred for 2.5 hours at room temperature. The mixture was adjusted to pH 4 with conc. hydrochloric acid under cooling and concentrated to 70 ml under reduced pressure. The aqueous solution was stood in a refrigerator for one hour and the resulting precipitates were collected by filtration, washed with cold water and dried to give methyl 2-carbamoyl-2-ethoxyiminoacetate (syn isomer) (31 g), mp 68° to 71° C.

Workup

  1. temperatureunder cooling
  2. concentrationconcentrated to 70 ml under reduced pressure
  3. waitThe aqueous solution was stood in a refrigerator for one hour
  4. customthe resulting precipitates
  5. filtrationwere collected by filtration
  6. washwashed with cold water
  7. customdried

Sources & evidence

ORD record
ord-9c969687cc41486ab8a0f21519c8fca0
Source dataset
uspto-grants-1985_06
Patent number
US04521413

Reaction notes

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