Phosphorus oxychloride → 4,8-Dichloro-2,3-dimethylquinoline

HRID 1431298Notes

Reaction equation

HRID 1431298 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([CH3:12])[C:8]([CH3:13])=[C:7]2O.P(Cl)(Cl)([Cl:17])=O>>[Cl:17][C:7]1[C:6]2[C:11](=[C:2]([Cl:1])[CH:3]=[CH:4][CH:5]=2)[N:10]=[C:9]([CH3:12])[C:8]=1[CH3:13]

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178432245HCID 178432245, compound

Product 1

HCID 596315464,8-Dichloro-2,3-dimethylquinoline

Procedure

A mixture of 8-chloro-2,3-dimethylquinolin-4-ol (1.83 g, 8.81 mmol) in phosphorous oxychloride (10.00 mL) was heated to reflux for 2 h, after which time LC-MS indicated only product present. The reaction solution was poured into ice and adjusted to pH>10. The aq. mixture was extracted with 2×75 mL DCM. The combined organic extracts were stirred over anhydrous magnesium sulfate, filtered and the filtrate concentrated under reduced pressure to afford a pale yellow solid, which was not further purified. Mass Spectrum (ESI) m/e=226.0 (M+1).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 2 h
  3. additionThe reaction solution was poured into ice
  4. extractionThe aq. mixture was extracted with 2×75 mL DCM
  5. filtrationfiltered
  6. concentrationthe filtrate concentrated under reduced pressure
  7. customto afford a pale yellow solid, which

Sources & evidence

ORD record
ord-362b9b65e86b4dd4aa1cf422a9f13eb2
Source dataset
uspto-grants-2015_01
Patent number
US08940724B2

Reaction notes

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