Pyridine → HCID 19068886, compound

HRID 1957129Notes

Reaction equation

HRID 1957129 reaction equation
S(Cl)([Cl:3])=O.[CH3:5][O:6][C:7]1[C:16]([O:17][CH3:18])=[N:15][C:14]2[C:9](=[CH:10][C:11]([CH3:22])=[C:12]([CH3:21])[C:13]=2[CH2:19]O)[N:8]=1.N1C=CC=CC=1>C1(C)C=CC=CC=1>[Cl:3][CH2:19][C:13]1[C:12]([CH3:21])=[C:11]([CH3:22])[CH:10]=[C:9]2[C:14]=1[N:15]=[C:16]([O:17][CH3:18])[C:7]([O:6][CH3:5])=[N:8]2

Participants

5

Reactant 3

HCID 1049PyridineHCID 24386Thionyl ChlorideHCID 19068900HCID 19068900, compound

Product 1

HCID 19068886HCID 19068886, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Thionyl chloride (0.44 mL, 6.0 mmol) was added dropwise to a solution of 2,3-dimethoxy-6,7-dimethyl-5-hydroxymethylquinoxaline (0.50 g, 2.0 mmol) in toluene (30 mL) and pyridine (0.81 mL, 10.0 mmol) under nitrogen at 5° C. After 20 minutes, water (20 mL), and the aqueous layer was extracted with ethyl acetate (2×20 mL). The combined organic solutions were washed with 2M hydrochloric acid, dried (MgSO4) and concentrated under reduced pressure. Purification of the residue by flash chromatography (eluting with dichloromethane) gave 5-(chloromethyl)-2,3-dimethoxy-6,7-dimethylquinoxaline (0.18 g, 34%) as a pale yellow solid.

Workup

  1. extractionwater (20 mL), and the aqueous layer was extracted with ethyl acetate (2×20 mL)
  2. washThe combined organic solutions were washed with 2M hydrochloric acid
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated under reduced pressure
  5. customPurification of the residue
  6. washby flash chromatography (eluting with dichloromethane)

Sources & evidence

ORD record
ord-254dd89bf3374228be3d1bfff700549e
Source dataset
uspto-grants-1998_07
Patent number
US05783572

Reaction notes

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