Methyl acetoacetate → HCID 70611054, compound

HRID 1678877Notes

Reaction equation

HRID 1678877 reaction equation
[CH2:1]([N:3]1[CH2:7][CH2:6][CH2:5][CH:4]1[CH2:8][NH2:9])[CH3:2].[2H]Cl.[C:12]([O:18][CH3:19])(=[O:17])[CH2:13][C:14]([CH3:16])=O.S([O-])([O-])(=O)=O.[Mg+2]>C(Cl)Cl>[CH2:1]([N:3]1[CH2:7][CH2:6][CH2:5][CH:4]1[CH2:8][NH:9]/[C:14](/[CH3:16])=[CH:13]\[C:12]([O:18][CH3:19])=[O:17])[CH3:2]

Participants

6

Reactant 4

HCID 7757Methyl acetoacetateHCID 24083Sulfuric acid magnesium salt (1:1)HCID 1172952-Aminomethyl-1-ethylpyrrolidineHCID 522634Deuterium chloride

Product 1

HCID 70611054HCID 70611054, compoundYield 81.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

38.4 G (0.3 MOLE) OF N-ethyl-2-aminomethylpyrrolidine and a drop of hydrochloric acid d = 1.18 were added into a 250 ml flask provided with a stirrer, a thermometer, a condenser and a dropping funnel; 38.4 g (0.3 mole) of methyl acetoacetate were added drop by drop. The temperature reached 54° C by the end of the introduction. The mixture was next allowed to return to ambient temperature while stirring, and 150 ml of methylene chloride and 5 g of magnesium sulphate were then added. The mixture was stirred for one hour, filtered, the solvent was evaporated in vacuo, and the residue was distilled. 55 g of methyl N-(1-ethyl-2-pyrrolidylmethyl)-3-aminocrotonate were obtained. (Yield: 81.1%; boiling point - 3 mm/Hg: 132°-134° C).

Workup

  1. customprovided with a stirrer
  2. customreached 54° C by the end of the introduction
  3. customto return to ambient temperature
  4. stirringThe mixture was stirred for one hour
  5. filtrationfiltered
  6. customthe solvent was evaporated in vacuo
  7. distillationthe residue was distilled

Sources & evidence

ORD record
ord-69383cba832e4e17854012455eae56bf
Source dataset
uspto-grants-1978_03
Patent number
US04077976

Reaction notes

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