Water → HCID 59857982, compound

HRID 2378158Notes

Reaction equation

HRID 2378158 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 recrystalized 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. customrecrystalized from CHCl3-hexanes

Sources & evidence

ORD record
ord-70ccf485d09844b6ab844e2cc4d44ada
Source dataset
uspto-grants-2008_12
Patent number
US07470788B2

Reaction notes

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