Phosphorus oxychloride → 2-Chloroquinolin-8-ol

HRID 1777140Notes

Reaction equation

HRID 1777140 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[OH:11])[CH:4]=[CH:3][C:2]=1O.O=P(Cl)(Cl)[Cl:15]>>[Cl:15][C:2]1[CH:3]=[CH:4][C:5]2[C:10](=[C:9]([OH:11])[CH:8]=[CH:7][CH:6]=2)[N:1]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178515617HCID 178515617, compound

Product 1

HCID 2748782-Chloroquinolin-8-olYield 70%

Conditions

Temperature
100 °C

Procedure

To a stirred mixture of quinoline-2,8-diol (1 g, 6.21 mmol) was added POCl3 (10 mL) and the mixture stirred at 100° C. for 1 hour before cooling. The mixture was then poured into ice-water (100 mL) slowly and filtered. The collected solid was dried and used in next step without further purification. (780 mg, Yield 70%). 1H NMR (400 MHz, DMSO-d6) δ 8.39 (d, J=8.8 Hz, 1H), 7.57 (d, J=8.8 Hz, 1H), 7.48-7.43 (m, 2H), 7.17 (dd, J1=8.8 Hz, J1=1.6 Hz, 1H).

Workup

  1. temperaturebefore cooling
  2. filtrationfiltered
  3. customThe collected solid was dried
  4. customused in next step without further purification

Sources & evidence

ORD record
ord-a2a50377c7d44f2b82e841bc8dbecc51
Source dataset
uspto-grants-2016_02
Patent number
US09266836B2

Reaction notes

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