Phosphorus oxychloride → 4-Chloro-3-(2-chloroethyl)cinnoline

HRID 704567Notes

Reaction equation

HRID 704567 reaction equation
[Cl:1][CH2:2][CH2:3][C:4]1[C:13](=O)[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][N:5]=1.P(Cl)(Cl)([Cl:17])=O>>[Cl:1][CH2:2][CH2:3][C:4]1[N:5]=[N:6][C:7]2[C:12]([C:13]=1[Cl:17])=[CH:11][CH:10]=[CH:9][CH:8]=2

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 200727583-(2-Chloroethyl)-4-oxo-(1H)-cinnoline

Product 1

HCID 200727524-Chloro-3-(2-chloroethyl)cinnoline

Procedure

3-(2-Chloroethyl)-4-oxo-(1H)-cinnoline (9 g, 0.043 mol) and phosphorus oxychloride (90 ml) were heated under reflux for 1 hour. After allowing to cool, the excess phosphorus oxychloride was evaporated under reduced pressure and the residue was poured onto ice (100 g), basified with concentrated ammonia solution, and extracted with chloroform (3×100 ml). The chloroform extracts were combined, dried over magnesium sulphate and evaporated under reduced pressure to give a solid, 8.00 g. Recrystallization from diethyl ether gave the title compound, m.p. 81-82°.

Workup

  1. temperatureunder reflux for 1 hour
  2. temperatureto cool
  3. customthe excess phosphorus oxychloride was evaporated under reduced pressure
  4. additionthe residue was poured onto ice (100 g)
  5. extractionextracted with chloroform (3×100 ml)
  6. dry with materialdried over magnesium sulphate
  7. customevaporated under reduced pressure
  8. customto give a solid, 8.00 g
  9. customRecrystallization from diethyl ether

Sources & evidence

ORD record
ord-d075416f26954eb8b0f827581e8b9a58
Source dataset
uspto-grants-1991_01
Patent number
US04988695

Reaction notes

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