Potassium Carbonate → HCID 73554558, compound

HRID 81016Notes

Reaction equation

HRID 81016 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][NH:12][C:11](=O)[C:10]=2[C:16]#[N:17])=[CH:5][CH:4]=1.P(Cl)(Cl)([Cl:20])=O.C(=O)(O)[O-].[Na+].C(=O)([O-])[O-].[K+].[K+]>C(OCC)(=O)C>[Cl:20][C:11]1[N:12]=[CH:13][CH:14]=[C:9]([C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[C:10]=1[C:16]#[N:17]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 669269194-(4-Methoxyphenyl)-2-oxo-1,2-dihydropyridine-3-carbonitrile

Product 1

HCID 73554558HCID 73554558, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 4-(4-methoxyphenyl)-2-oxo-1,2-dihydropyridine-3-carbonitrile (1.00 g, 4.42 mmol) and phosphoryl trichloride (8 mL, 87 mmol) was heated to 110° C. for 15 h. The mixture was diluted with ethyl acetate (100 mL), carefully treated with saturated sodium bicarbonate (100 mL), neutralized to pH˜7 with careful addition of solid potassium carbonate while stirring vigorously, and extracted with ethyl acetate (3×100 mL). The combined extracts were washed with brine (40 mL), dried (MgSO4) and concentrated to give 2-chloro-4-(4-methoxyphenyl)nicotinonitrile as a brown solid (960 mg, 89% yield). 1H NMR (400 MHz, CDCl3) δ ppm 8.54 (1H, δ, J=5.27 Hz), 7.48-7.82 (2H, m), 7.38 (1H, δ, J=5.27 Hz), 6.94-7.18 (2H, m), 3.90 (3H, s); MS (ES+) m/z: 245 (M+H); LC retention time: 3.303 min (analytical HPLC Method A).

Workup

  1. extractionextracted with ethyl acetate (3×100 mL)
  2. washThe combined extracts were washed with brine (40 mL)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-722845eb109e497c90ed6e2b1e98327a
Source dataset
uspto-grants-2014_09
Patent number
US08846673B2

Reaction notes

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