Phosphorus oxychloride → HCID 178426119, compound

HRID 2206480Notes

Reaction equation

HRID 2206480 reaction equation
[OH:1][C:2]1[N:9]=[C:8]([CH3:10])[CH:7]=[C:6](O)[C:3]=1[C:4]#[N:5].P(Cl)(Cl)([Cl:14])=O>C(#N)C.[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1>[Cl:14][C:6]1[C:3]([C:4]#[N:5])=[C:2]([OH:1])[N:9]=[C:8]([CH3:10])[CH:7]=1

Participants

5

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178429083HCID 178429083, compound

Product 1

HCID 178426119HCID 178426119, compoundYield 48%

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 6342AcetonitrileSolvent

Procedure

To a solution of 2,4-dihydroxy-6-methylnicotinonitrile (1.5 g, 10 mmol) in acetonitrile (50 mL) was added benzyltriethylammonium chloride (9.1 g, 40 mmol) and phosphorus oxychloride (6.13 g, 40 mmol). The resulting mixture was stirred for 4 hours at room temperature. The solvent was removed by rotary evaporation. To the residue was added dichloromethane (100 mL) and water (50 mL). The organic phase was separated, washed with brine (50 mL), dried over anhydrous magnesium sulfate, filtered and concentrated to give crude product which was purified by column chromatography (silica gel, petroleum ether/ethyl acetate=4:1) to afford 4-chloro-2-hydroxy-6-methylnicotinonitrile (800 mg, 48%) as a brown solid.

Workup

  1. customThe solvent was removed by rotary evaporation
  2. additionTo the residue was added dichloromethane (100 mL) and water (50 mL)
  3. customThe organic phase was separated
  4. washwashed with brine (50 mL)
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give crude product which
  9. customwas purified by column chromatography (silica gel, petroleum ether/ethyl acetate=4:1)

Sources & evidence

ORD record
ord-1726d2d461f94a6baecfcbcc296580c1
Source dataset
uspto-grants-2016_06
Patent number
US09371331B2

Reaction notes

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