Phosphorus oxychloride → 8-(Benzyloxy)-2-chloroquinoline

HRID 1777172Notes

Reaction equation

HRID 1777172 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][CH:12]=[C:13]2[C:18]=1[N:17]=[C:16](O)[CH:15]=[CH:14]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O=P(Cl)(Cl)[Cl:22]>>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][CH:12]=[C:13]2[C:18]=1[N:17]=[C:16]([Cl:22])[CH:15]=[CH:14]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178515619HCID 178515619, compound

Product 1

HCID 220422348-(Benzyloxy)-2-chloroquinolineYield 85%

Conditions

Temperature
90 °C

Procedure

8-(benzyloxy)quinolin-2-ol (6.6 g, 26.3 mmol) was dissolved in POCl3 (50 mL). The mixture was stirred at 90° C. for 16 h. The POCl3 was evaporated and to the residue was added EtOAc (100 mL) and the solution was washed with a.q. NaHCO3 (80 mL) and H2O (80 mL). The EtOAc was removed under vacuum to give the desired compound (6.0 g, yield 85%). LCMS (m/z): 270.1 [M+H]+

Workup

  1. customThe POCl3 was evaporated and to the residue
  2. additionwas added EtOAc (100 mL)
  3. washthe solution was washed with a.q
  4. customThe EtOAc was removed under vacuum

Sources & evidence

ORD record
ord-fb616de908884d78bb8380893a5ff4d4
Source dataset
uspto-grants-2016_02
Patent number
US09266836B2

Reaction notes

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