Methyl chloroacetate → HCID 13174340, compound

HRID 1615623Notes

Reaction equation

HRID 1615623 reaction equation
[NH2:1][N:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]1=[NH2+:8].CC1C=C(C)C=C(C)C=1S([O-])(=O)=O.[OH-].[Na+].[Cl:24][CH2:25][C:26](OC)=O>CCO>[Cl:24][CH2:25][C:26]1[N:8]=[C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][N:2]2[N:1]=1

Participants

5

Reactant 3

HCID 7295Methyl chloroacetateHCID 14798Sodium HydroxideHCID 178425983HCID 178425983, compound

Product 1

HCID 13174340HCID 13174340, compoundYield 29%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 1-aminopyridin-2(1H)-iminium-2,4,6-trimethylbenzenesulfonate (crude product from the previous step) and sodium hydroxide (NaOH) (0.55 g, 13.8 mmol) in EtOH (30 mL) was stirred at 60° C. for 1 h, then methyl 2-chloroacetate (1.12 g, 10.4 mmol) was added. The reaction mixture was refluxed for 4 h, then the solvent was removed. The product was purified by silica gel column chromatography (eluting with 20% v/v EtOAc in PE) to give the title compound (512 mg, yield: 29%, 2 steps). ESI MS: m/z 168 [M+H]+.

Workup

  1. temperatureThe reaction mixture was refluxed for 4 h
  2. customthe solvent was removed
  3. customThe product was purified by silica gel column chromatography (
  4. washeluting with 20% v/v EtOAc in PE)

Sources & evidence

ORD record
ord-c24ba078bb83499ebfc0ce8da74c7b85
Source dataset
uspto-grants-2014_07
Patent number
US08765760B2

Reaction notes

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