Methanol → HCID 22710914, compound

HRID 352786Notes

Reaction equation

HRID 352786 reaction equation
Cl.[CH3:2][C:3]1[CH:8]=[C:7]([C:9]2[CH:17]=[CH:16][C:12]([C:13]([OH:15])=[O:14])=[CH:11][CH:10]=2)[CH:6]=[CH:5][N:4]=1.S(Cl)([Cl:20])=O.[CH3:22]O>>[ClH:20].[CH3:2][C:3]1[CH:8]=[C:7]([C:9]2[CH:17]=[CH:16][C:12]([C:13]([O:15][CH3:22])=[O:14])=[CH:11][CH:10]=2)[CH:6]=[CH:5][N:4]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 67053024HCID 67053024, compound

Product 1

HCID 22710914HCID 22710914, compound

Procedure

In methanol (100 ml), 4-(2-methylpyridin-4-yl)benzoic acid hydrochloride (5.00 g) was dissolved. To the resulting solution, thionyl chloride (1.73 ml) was added dropwise, followed by heating under reflux for 3.5 hours. The reaction mixture was distilled to remove the solvent and pale brown crystals thus precipitated were washed with ethyl acetate, whereby the title compound (4.70 g, 89%) was obtained.

Workup

  1. temperatureby heating
  2. temperatureunder reflux for 3.5 hours
  3. distillationThe reaction mixture was distilled
  4. customto remove the solvent and pale brown crystals
  5. customthus precipitated
  6. washwere washed with ethyl acetate, whereby the title compound (4.70 g, 89%)
  7. customwas obtained

Sources & evidence

ORD record
ord-5ec84662694e4045820b43e757d2e59b
Source dataset
uspto-grants-2004_06
Patent number
US06747023B1

Reaction notes

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