Hydrochloric Acid → HCID 69673238, compound

HRID 2276345Notes

Reaction equation

HRID 2276345 reaction equation
[NH2:1][C:2]1[C:11]([C:12]#N)=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[C:14]1([CH3:22])[CH:19]=[CH:18][C:17]([Mg]Br)=[CH:16][CH:15]=1.Cl.[OH-:24].[Na+]>O1CCCC1>[NH2:1][C:2]1[C:11]([C:12]([C:17]2[CH:18]=[CH:19][C:14]([CH3:22])=[CH:15][CH:16]=2)=[O:24])=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 2685052-aminoquinoline-3-carbonitrileHCID 178418370HCID 178418370, compound

Product 1

HCID 69673238HCID 69673238, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-aminoquinoline-3-carbonitrile (1.86 g; 11 mmol) in dry tetrahydrofurane (110 mL) under a nitrogen atmosphere was slowly added a solution of p-tolylmagnesium bromide (1M in THF) (55 mL; 55 mmol). The resulting solution was stirred at room temperature for 4 h. A solution of hydrochloric acid 3N (220 mL) was added to hydrolyse the intermediate imine and the reaction mixture was heated to reflux for 2 h and then stirred at room temperature for 18 h. After cooling to 0° C., the reaction mixture was basified with a solution of sodium hydroxide 6N. The product was extracted with ethyl acetate (160 mL) and the organics were dried over sodium sulfate, filtered and concentrated under reduced pressure. Purification by flash-chromatography on silica gel using a gradient of ethyl acetate (5-100%) in dichloromethane as eluent furnished 2.6 g (90%) of (2-aminoquinolin-3-yl)(p-tolyl)methanone as an ochre solid. ESI/APCI(+): 263 (M+H).

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureto reflux for 2 h
  3. stirringstirred at room temperature for 18 h
  4. temperatureAfter cooling to 0° C.
  5. extractionThe product was extracted with ethyl acetate (160 mL)
  6. dry with materialthe organics were dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customPurification by flash-chromatography on silica gel using a gradient of ethyl acetate (5-100%) in dichloromethane as eluent

Sources & evidence

ORD record
ord-1c00ea3d76254a2e82128ea8d36f474d
Source dataset
uspto-grants-2015_09
Patent number
US09132129B2

Reaction notes

Loading…