Phosphorus oxychloride → 2,6-Dichloroquinoline

HRID 1253914Notes

Reaction equation

HRID 1253914 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7](O)[CH:6]=[CH:5]2.O=P(Cl)(Cl)[Cl:15]>>[Cl:15][C:7]1[CH:6]=[CH:5][C:4]2[C:9](=[CH:10][CH:11]=[C:2]([Cl:1])[CH:3]=2)[N:8]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178515629HCID 178515629, compound

Product 1

HCID 6075022,6-DichloroquinolineYield 90%

Procedure

180 mg 6-chloro-2-hydroxy quinoline was treated by 3 ml POCl3, the mixture was refluxed for 3 hours, the remaining POCl3 was evaporated out. After cooling to room temperature, the residue was treated by cold water, the solid was filtered out and dried as green powder, yield: 90%. Following the general procedure in claim 5, the listed compounds were achieved. Mass calculated for C9H5Cl2N: 198; LCMS: 200.1 (M+2)+; 1HNMR (400 MHZ), DMSO-d6) δ ppm 8.04 (1H, d, J=7.8 Hz), 7.97 (1H, d, J=8.8 Hz), 7.81 (1H, d, J=1.9 Hz), 7.68 (1H, dd, J=9.8 Hz, J=2.9 Hz), 7.42 (1H, d, J=8.8 Hz).

Workup

  1. temperaturethe mixture was refluxed for 3 hours
  2. customthe remaining POCl3 was evaporated out
  3. additionthe residue was treated by cold water
  4. filtrationthe solid was filtered out
  5. customdried as green powder, yield: 90%

Sources & evidence

ORD record
ord-8ab2125dfc3e4565887e933bdb194c31
Source dataset
uspto-grants-2013_06
Patent number
US08455516B2

Reaction notes

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