Acetic Acid → HCID 86644237, compound

HRID 451336Notes

Reaction equation

HRID 451336 reaction equation
[Cl:1][CH2:2][C:3](=O)[CH2:4]C(OCC)=O.[C:11]([OH:14])(=[O:13])[CH3:12].[Cl:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22][NH2:23])=[CH:18][N:17]=1.[C:24]1(C)C=CC=C[CH:25]=1>C(O)C>[Cl:1][CH2:2][C:3]([NH:23][CH2:22][C:19]1[CH:18]=[N:17][C:16]([Cl:15])=[CH:21][CH:20]=1)=[CH:4][CH2:12][C:11]([O:14][CH2:24][CH3:25])=[O:13]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 1140TolueneHCID 69484Ethyl 4-chloroacetoacetateHCID 70209275-(Aminomethyl)-2-chloropyridine

Product 1

HCID 86644237HCID 86644237, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2.1 g of ethyl 4-chloroacetoacetate in 12 ml of toluene is added 0.15 ml of acetic acid. At 10° C.-30° C., with cooling, 2 g of 2-chloro-5-(aminomethyl)pyridine dissolved in 4 ml of 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. 4.2 g of ethyl 4-chloro-3-([[6-chloropyridin-3-yl]methyl]amino)but-2-enecarboxylate are obtained in a purity of 86% (this corresponds to 98% yield).

Workup

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

Sources & evidence

ORD record
ord-7faf10a9caa946ffb0dc796bdeda86eb
Source dataset
uspto-grants-2013_07
Patent number
US08487112B2

Reaction notes

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