Sodium Chloride → HCID 59233032, compound

HRID 1925160Notes

Reaction equation

HRID 1925160 reaction equation
[Cl:1][C:2]1[N:7]=[N:6][C:5]([C:8](C)([C:14](OCC)=O)[C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:4][CH:3]=1.[Na+].[Cl-]>CS(C)=O.O>[Cl:1][C:2]1[N:7]=[N:6][C:5]([CH:8]([CH3:14])[C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 5234Sodium ChlorideHCID 59233051HCID 59233051, compound

Product 1

HCID 59233032HCID 59233032, compoundYield 35.2%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
175 °C

Procedure

A solution of diethyl 2-(6-chloropyridazin-3-yl)-2-methylmalonate (11 g, 38.4 mmol) and NaCl (2.69 g, 46.0 mmol) in DMSO (91 mL) and H2O (1.382 ml) was divided into eight separate microwave vials and each reaction was heated in a microwave at 175° C. for 90 mins on high absorbance. The reactions were combined and then poured into H2O (300 mL). The aqueous phase was extracted with EtOAc (2×100 mL) and then the organic phase was washed with brine (2×100 mL). The organic phase was dried over MgSO4, filtered and concentrated to dryness via rotary evaporation. The resulting oil was purified via MPLC (3:1, Hex:EtOAc) to provide the title compound, ethyl 2-(6-chloropyridazin-3-yl)propanoate (54A, 2.9 g, 35%). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.13 (s, 3 H) 1.49 (d, J=7.33 Hz, 3 H) 4.09 (dd, J=7.07, 2.02 Hz, 2 H) 4.23 (d, J=7.33 Hz, 1 H) 7.83 (d, J=8.84 Hz, 1 H) 7.93 (d, J=8.84 Hz, 1 H). ESI-MS:m/z 215.0 (M+H)+.

Workup

  1. customseparate microwave vials
  2. additionpoured into H2O (300 mL)
  3. extractionThe aqueous phase was extracted with EtOAc (2×100 mL)
  4. washthe organic phase was washed with brine (2×100 mL)
  5. dry with materialThe organic phase was dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated to dryness via rotary evaporation
  8. customThe resulting oil was purified via MPLC (3:1, Hex:EtOAc)

Sources & evidence

ORD record
ord-23ba8594e12e49fd975fb287b6b56a2d
Source dataset
uspto-grants-2012_05
Patent number
US08178534B2

Reaction notes

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