Hydrochloric Acid → 2-(2,4-Dimethoxybenzoyl)-6-methylpyridine

HRID 2059736Notes

Reaction equation

HRID 2059736 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([C:8]#N)[CH:5]=[CH:4][CH:3]=1.[CH3:10][O:11][C:12]1[CH:17]=[C:16]([O:18][CH3:19])[CH:15]=[CH:14][C:13]=1[Mg]Br.Cl.C1C[O:26]CC1>>[CH3:10][O:11][C:12]1[CH:17]=[C:16]([O:18][CH3:19])[CH:15]=[CH:14][C:13]=1[C:8]([C:6]1[CH:5]=[CH:4][CH:3]=[C:2]([CH3:1])[N:7]=1)=[O:26]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 741826-Methylpyridine-2-carbonitrileHCID 178491918HCID 178491918, compound

Product 1

HCID 497619912-(2,4-Dimethoxybenzoyl)-6-methylpyridine

Conditions

Temperature
0 °C

Procedure

6-Methylpyridine-2-carbonitrile (4.88 g, 41.3 mmol) was dissolved in THF (50 mL), cooled to 0° C. and 2,4-dimethoxyphenylmagnesium bromide (20.5 mL, 10.24 mmol, 0.5 M in THF) was added. The reaction aged at rt for 3 h and was quenched with HCl (45.4 mL, 91 mmol, 2 M diethyl ether). The reaction was concentrated and extracted with EtOAc. The aq layer was basified to pH 10 and extracted with EtOAc. The combined organic portions were washed with brine, dried with Na2SO4, filtered and concentrated. The residue was purified by flash chromatography on silica gel gradient eluted with 0 to 50% EtOAc/hexane, affording the title compound. HPLC/MS: 258.3 (M+1); Rt=1.96 min.

Workup

  1. concentrationThe reaction was concentrated
  2. extractionextracted with EtOAc
  3. extractionextracted with EtOAc
  4. washThe combined organic portions were washed with brine
  5. dry with materialdried with Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by flash chromatography on silica gel gradient
  9. washeluted with 0 to 50% EtOAc/hexane

Sources & evidence

ORD record
ord-dd7076e24bea494ab39adb7309083c9b
Source dataset
uspto-grants-2012_10
Patent number
US08278304B2

Reaction notes

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