Benzoyl chloride, 3-chloro- → HCID 69195748, compound

HRID 2116516Notes

Reaction equation

HRID 2116516 reaction equation
C([Mg]Cl)(C)C.[Cl:6][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:16]=1[N:15]=[CH:14][C:13](I)=[CH:12]2.[Cu]C#N.[Cl:21][C:22]1[CH:23]=[C:24]([CH:28]=[CH:29][CH:30]=1)[C:25](Cl)=[O:26]>O1CCCC1>[Cl:21][C:22]1[CH:23]=[C:24]([C:25]([C:13]2[CH:14]=[N:15][C:16]3[C:11]([CH:12]=2)=[CH:10][CH:9]=[CH:8][C:7]=3[Cl:6])=[O:26])[CH:28]=[CH:29][CH:30]=1

Participants

6

Reactant 4

HCID 69252Benzoyl chloride, 3-chloro-HCID 534386358-Chloro-3-iodoquinolineHCID 178418546HCID 178418546, compoundHCID 178418918HCID 178418918, compound

Product 1

HCID 69195748HCID 69195748, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-40 °C

Procedure

iso-Propyl magnesium chloride (2M solution in tetrahydrofuran) (2.85 ml, 5.7 mmol) was added dropwise over 5 mins to a stirred solution of 8-chloro-3-iodoquinoline (D1)(1.5 g, 5.2 mmol) in tetrahydrofuran (15 ml) at −40° C. under argon. After stirring the solution at this temperature for 0.3 h, copper (I) cyanide (0.47 g, 5.2 mmol) was added in portions over 5 mins. The whole mixture was left to stir at −40° C. for a further 10 mins and then 3-chlorobenzoyl chloride (1.0 g, 5.7 mmol) was added dropwise over 10 mins. The temperature was maintained at −40° C. for 0.5 h and then the reaction was warmed to 0° C. at which temperature it was quenched by the addition of a saturated solution of sodium chloride (100 ml). The mixture was extracted with ethyl acetate (2×50 ml). The combined extracts were dried (MgSO4) and concentrated in vacuo to a solid. The solid was purified by chromatography over silica gel eluting with a gradient of acetone/toluene to give the title compound (D5) as a white solid (0.95 g, 3.1 mmol, 60%).

Workup

  1. waitThe whole mixture was left
  2. stirringto stir at −40° C. for a further 10 mins
  3. temperaturethe reaction was warmed to 0° C. at which temperature it
  4. customwas quenched by the addition of a saturated solution of sodium chloride (100 ml)
  5. extractionThe mixture was extracted with ethyl acetate (2×50 ml)
  6. dry with materialThe combined extracts were dried (MgSO4)
  7. concentrationconcentrated in vacuo to a solid
  8. customThe solid was purified by chromatography over silica gel eluting with a gradient of acetone/toluene

Sources & evidence

ORD record
ord-9a7ea7f24f324fb1811cabad842a311b
Source dataset
uspto-grants-2008_10
Patent number
US07439243B2

Reaction notes

Loading…