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

HRID 526161Notes

Reaction equation

HRID 526161 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-d13c883052814b55a1b77a395cbc21dc
Source dataset
uspto-grants-2016_05
Patent number
US09345709B2

Reaction notes

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