Methanol → Methyl 1-(6-chloro-3-pyridinyl)cyclopropanecarboxylate

HRID 1099048Notes

Reaction equation

HRID 1099048 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2([C:11]([OH:13])=[O:12])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.S(=O)(=O)(O)O.[CH3:19]O>>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2([C:11]([O:13][CH3:19])=[O:12])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 592163081-(6-Chloropyridin-3-yl)cyclopropane-1-carboxylic acid

Product 1

HCID 59216284Methyl 1-(6-chloro-3-pyridinyl)cyclopropanecarboxylateYield 93%

Conditions

Temperature
80 °C

Procedure

A mixture of 1-(6-chloropyridin-3-yl)cyclopropanecarboxylic acid (2.0 g, 0.010 mol) and sulfuric acid (0.42 mL, 0.0079 mol) in methanol (30 mL) was stirred at 80° C. for 6 h. The mixture was cooled to RT and concentrated. The residue was dissolved in saturated sodium bicarbonate and extracted with ethyl acetate. The organic layers were washed with brine, dried with Na2SO4, filtered, and concentrated under reduced pressure to give a crude product (2.0 g, 93%). Analytical LCMS: (M+H)+=212.0.

Workup

  1. temperatureThe mixture was cooled to RT
  2. concentrationconcentrated
  3. dissolutionThe residue was dissolved in saturated sodium bicarbonate
  4. extractionextracted with ethyl acetate
  5. washThe organic layers were washed with brine
  6. dry with materialdried with Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a214f747c83f4e9b8fee78b0da96aedf
Source dataset
uspto-grants-2012_03
Patent number
US08143251B2

Reaction notes

Loading…