Trimethylbenzylammonium Dichloroiodate → 2-Chloro-1-(4,6-dichloro-1,5-naphthyridin-3-yl)ethanone

HRID 2178882Notes

Reaction equation

HRID 2178882 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([Cl:12])[N:10]=2)[N:5]=[CH:4][C:3]=1[C:13](=[O:15])[CH3:14].I([Cl:19])(=O)=O.I(Cl)(=O)=O.C([N+](C)(C)C)C1C=CC=CC=1>C1COCC1>[Cl:19][CH2:14][C:13]([C:3]1[CH:4]=[N:5][C:6]2[C:11]([C:2]=1[Cl:1])=[N:10][C:9]([Cl:12])=[CH:8][CH:7]=2)=[O:15]

Participants

4

Reactant 2

HCID 56924451Trimethylbenzylammonium DichloroiodateHCID 897049771-(4,6-Dichloro-1,5-naphthyridin-3-yl)ethan-1-one

Product 1

HCID 897054772-Chloro-1-(4,6-dichloro-1,5-naphthyridin-3-yl)ethanoneYield 33.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 1-(4,6-dichloro-1,5-naphthyridin-3-yl)ethanone (3.0 g, 12 mmol) in THF (120 mL) was added benzyltrimethylammonium dichloroiodate (4.3 g, 12 mmol) and the reaction mixture was stirred at 70° C. for 5 h. The reaction mixture was cooled, diluted with satd. aq. sodium bicarbonate and extracted with dichloromethane. The combined organic layers were dried over anhydrous sodium sulfate, filtered and the filtrate was concentrated. The residue was purified by column chromatography (silica, dichloromethane/ethyl acetate) to afford the desired product (1.1 g, 32%) as an off-white solid. ESI MS m/z 275 [M+H]+.

Workup

  1. temperatureThe reaction mixture was cooled
  2. additiondiluted with satd
  3. extractionaq. sodium bicarbonate and extracted with dichloromethane
  4. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated
  7. customThe residue was purified by column chromatography (silica, dichloromethane/ethyl acetate)

Sources & evidence

ORD record
ord-b8f727e5c2c6414096f99dedcd9b69dd
Source dataset
uspto-grants-2015_06
Patent number
US09067937B2

Reaction notes

Loading…