Water → HCID 59857982, compound

HRID 1928552Notes

Reaction equation

HRID 1928552 reaction equation
[Cl:1][C:2]1[C:11]([O:12][CH3:13])=[C:10]2[C:5]([CH:6]=[CH:7][C:8](O)=[N:9]2)=[CH:4][CH:3]=1.O=P(Cl)(Cl)[Cl:17].O.C([O-])(O)=O.[Na+]>CCOC(C)=O>[Cl:17][C:8]1[CH:7]=[CH:6][C:5]2[C:10](=[C:11]([O:12][CH3:13])[C:2]([Cl:1])=[CH:3][CH:4]=2)[N:9]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 178492962HCID 178492962, compound

Product 1

HCID 59857982HCID 59857982, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

7-Chloro-8-methoxy-2-quinolinol (4b) (2.85 g, 13.6 mmol) was mixed with POCl3 (6 mL) and allowed to reflux for 1.5 hours. To the concentrated contents, H2O and AcOEt were added followed by NaHCO3 to neutralize the mixture. The water layer was extracted with AcOEt, washed with saturated NaCl and dried with MgSO4. The product was filtered through silica gel using CHCl3 and recrystallized from CHCl3-hexanes to afford the desired product as off white crystals (2.53 g, 82% yield): mp 103-104 □C; 1H NMR (400 MHz, CDCl3) 8.07 (d, J=8.0 Hz, 1H), 7.54 (d, J=8.8 Hz, 1H), 7.50 (d, J=8.0 Hz, 1H), 7.39 (d, J=8.8 Hz, 1H), 4.19 (s, 3H).

Workup

  1. temperatureto reflux for 1.5 hours
  2. extractionThe water layer was extracted with AcOEt
  3. washwashed with saturated NaCl
  4. dry with materialdried with MgSO4
  5. filtrationThe product was filtered through silica gel
  6. customrecrystallized from CHCl3-hexanes

Sources & evidence

ORD record
ord-b450c62b63e8468585e6d30b6065f392
Source dataset
uspto-grants-2012_05
Patent number
US08183379B2

Reaction notes

Loading…