Hydrochloric Acid → HCID 178501737, compound

HRID 1069196Notes

Reaction equation

HRID 1069196 reaction equation
[C:1]([O:7][CH3:8])(=[O:6])[CH2:2][C:3]([CH3:5])=[O:4].[N:9]([O-])=[O:10].[Na+].Cl.O>C(OCC)C>[OH:10][N:9]=[C:2]([C:3]([CH3:5])=[O:4])[C:1]([O:7][CH3:8])=[O:6]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 7757Methyl acetoacetateHCID 23668193Sodium Nitrite

Product 1

HCID 178501737HCID 178501737, compoundYield 86.3%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 46.45 g (0.4 mol) of methyl acetoacetate in 200 ml of diethylether, 30.4 g (0.44 mol) of sodium nitrite was added and the mixture was cooled in an ice bath and treated dropwise with 40 ml (0.48 mol) of a concentrated hydrochloric acid. After stirring for 1 hour at room temperature, 200 ml of water was added and the mixture was extracted three times with 200 ml of diethylether. After washing with water and a saturated aqueous sodium chloride followed by drying over with anhydrous magnesium sulfate, the solvent was distilled off to obtain 50.09 g (yield: 86%) of a crude methyl 2-hydroxyiminoacetoacetate as a pale yellow oil. (2) Synthesis of methyl 2-benzyloxyiminoacetoacetate

Workup

  1. temperaturethe mixture was cooled in an ice bath
  2. extractionthe mixture was extracted three times with 200 ml of diethylether
  3. washAfter washing with water
  4. dry with materialby drying over with anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-bcef025ba5254578b4afb2f48e9e90fd
Source dataset
uspto-grants-2001_06
Patent number
US06251949B1

Reaction notes

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