Acetic Acid → HCID 86644230, compound

HRID 451328Notes

Reaction equation

HRID 451328 reaction equation
[Cl:1][CH2:2][C:3](=O)[CH2:4]C(OCC)=O.[C:11]([OH:14])(=[O:13])[CH3:12].[CH3:15][NH2:16].[C:17]1([CH3:23])C=CC=CC=1>C(O)C>[Cl:1][CH2:2][C:3]([NH:16][CH3:15])=[CH:4][CH2:12][C:11]([O:14][CH2:17][CH3:23])=[O:13]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 1140TolueneHCID 6329MethylamineHCID 69484Ethyl 4-chloroacetoacetate

Product 1

HCID 86644230HCID 86644230, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a solution of 300 of ethyl 4-chloroacetoacetate in 519 ml of toluene and 200 ml of ethanol are added 20.8 ml of acetic acid. At 10° C.-30° C., with cooling, 188.7 g of a 33% methylamine solution in ethanol are added dropwise. Subsequently, the mixture is stirred at room temperature for 8 h and the solvent is removed under reduced pressure at temperatures of down to 35° C. 328 g of ethyl 4-chloro-3-(methylamino)but-2-enecarboxylate are obtained in a purity of 91% (this corresponds to 92% yield).

Workup

  1. temperatureAt 10° C.-30° C., with cooling
  2. customthe solvent is removed under reduced pressure at temperatures of down to 35° C

Sources & evidence

ORD record
ord-bbc57b59f79143808d53312bca74def6
Source dataset
uspto-grants-2013_07
Patent number
US08487112B2

Reaction notes

Loading…