Ethyl 3-chloro-3-oxopropionate → HCID 67239641, compound

HRID 473416Notes

Reaction equation

HRID 473416 reaction equation
[NH2:1][C:2]1[C:3]([C:8]([O:10][CH3:11])=[O:9])=[N:4][CH:5]=[CH:6][CH:7]=1.Cl[C:13](=[O:20])[CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16]>ClC(Cl)C>[CH2:18]([O:17][C:15](=[O:16])[CH2:14][C:13]([NH:1][C:2]1[C:3]([C:8]([O:10][CH3:11])=[O:9])=[N:4][CH:5]=[CH:6][CH:7]=1)=[O:20])[CH3:19]

Participants

4

Reactant 2

HCID 118931Ethyl 3-chloro-3-oxopropionateHCID 9898880Methyl 3-aminopicolinate

Product 1

HCID 67239641HCID 67239641, compound

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

To a stirred solution of methyl 3-aminopicolinate (1.8 mL, 13.80 mmol) in dichloroethane (60 mL) was added ethyl 3-chloro-3-oxopropanoate (2.08 g, 13.80 mmol). The reaction was heated at reflux for 45 min. After this time the reaction was cooled to rt and partitioned between DCM (60 mL) and NaHCO3 (satd aq. solution, 30 mL). The separated aq. layer was extracted with DCM (40 mL) and the combined organic layer were washed with brine (20 mL), dried over MgSO4, filtered and concentrated in vacuo to give methyl 3-(3-ethoxy-3-oxopropanamido)picolinate: LC-MS (ESI) m/z 267.1 [M+H]+.

Workup

  1. temperatureThe reaction was heated
  2. temperatureat reflux for 45 min
  3. custompartitioned between DCM (60 mL) and NaHCO3 (satd aq. solution, 30 mL)
  4. extractionThe separated aq. layer was extracted with DCM (40 mL)
  5. washthe combined organic layer were washed with brine (20 mL)
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c1e67d23e8ed47b2baa89056a8d4f5d2
Source dataset
uspto-grants-2014_01
Patent number
US08633313B2

Reaction notes

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