Phosphorus oxychloride → HCID 59380854, compound

HRID 2354137Notes

Reaction equation

HRID 2354137 reaction equation
[C:1]1([C:7]2[C:8](O)=[N:9][C:10]3[C:15]([CH:16]=2)=[N:14][CH:13]=[CH:12][CH:11]=3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O=P(Cl)(Cl)[Cl:20]>CC#N.C([O-])(O)=O.[Na+]>[Cl:20][C:8]1[C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[CH:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][N:14]=2)[N:9]=1

Participants

5

Reactant 2

HCID 24813Phosphorus oxychloride3×HCID 178517241HCID 178517241, compound

Product 1

HCID 59380854HCID 59380854, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
0 °C

Procedure

3-Phenyl-1,5-naphthyridin-2-ol (3-4; 110 mg, 0.50 mmole) was taken up in CH3CN (3 mL). To this was added POCl3 (0.07 mL, 0.74 mmole) then the mixture was heated to reflux. After 3 hr POCl3 (0.07 mL, 0.74 mmole) was added and heating continued. After 3 hr POCl3 (0.15 mL) was added and heating continued. After 18 hr the mixture was cooled to 0° C. and diluted with saturated NaHCO3. After 15 min the mixture was warmed to RT and extracted with EtOAc (3×). The combined organic layers were dried (MgSO4), filtered through a plug of silica gel, and concentrated to give the title compound (3-5) as a light yellow solid: 1H-NMR (500 MHz, CDCl3) δ 9.02 (m, 1H), 8.38 (m, 2H), 7.69 (m, 1H), 7.59-7.49 (m, 5H).

Workup

  1. temperaturethe mixture was heated to reflux
  2. temperatureheating
  3. temperatureheating
  4. temperatureAfter 15 min the mixture was warmed to RT
  5. extractionextracted with EtOAc (3×)
  6. dry with materialThe combined organic layers were dried (MgSO4)
  7. filtrationfiltered through a plug of silica gel
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-5d2213e14df0426fa928dc7ec91d52f7
Source dataset
uspto-grants-2010_07
Patent number
US07750151B2

Reaction notes

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