Phosphorus oxychloride → HCID 59830723, compound

HRID 2424909Notes

Reaction equation

HRID 2424909 reaction equation
[CH2:1]([C:5]1[NH:6][C:7](=O)[CH:8]=[CH:9][C:10]=1[C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH2:2][CH2:3][CH3:4].P(Cl)(Cl)([Cl:19])=O>>[CH2:1]([C:5]1[N:6]=[C:7]([Cl:19])[CH:8]=[CH:9][C:10]=1[C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH2:2][CH2:3][CH3:4]

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 59830652HCID 59830652, compound

Product 1

HCID 59830723HCID 59830723, compoundYield 81%

Conditions

Temperature
120 °C

Procedure

Ethyl 2-butyl-6-oxo-1,6-dihydropyridine-3-carboxylate (450 mg, 2.02 mmol) was stirred in phosphorous oxychloride (10 ml, 30.5 mmol) and heated to 120° C. for 2 hours giving a clear brown solution. The reaction was evaporated and the residue was taken up in EtOAc (25 ml), washed with water (25 ml), saturated brine (25 ml) then dried over MgSO4 filtered and evaporated. Chromatography of the residue (SiO2) eluting with ethyl acetate/isohexane 10-30% gave ethyl 2-butyl-6-chloronicotinate (395 mg, 81%) as a clear oil.

Workup

  1. customgiving a clear brown solution
  2. customThe reaction was evaporated
  3. washwashed with water (25 ml), saturated brine (25 ml)
  4. dry with materialthen dried over MgSO4
  5. filtrationfiltered
  6. customevaporated
  7. washChromatography of the residue (SiO2) eluting with ethyl acetate/isohexane 10-30%

Sources & evidence

ORD record
ord-d68f0d4cd0664e25960acd8f47a2021d
Source dataset
uspto-grants-2011_06
Patent number
US07964618B2

Reaction notes

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