2,6-Lutidine → HCID 22667816, compound

HRID 1007124Notes

Reaction equation

HRID 1007124 reaction equation
[Cl:1][C:2]1[N:12]2[C:13]3[C:8]([C:9](=[O:14])[CH2:10][CH2:11]2)=[CH:7][CH:6]=[CH:5][C:4]=3[N:3]=1.[F-].[K+].[N:17]1[C:22](C)=[CH:21][CH:20]=[CH:19][C:18]=1C>CN(C)C=O>[Cl-:1].[CH3:2][N+:12]1([CH:20]2[CH2:19][CH2:18][N:17]([C:2]3[N:12]4[C:13]5[C:8]([C:9](=[O:14])[CH2:10][CH2:11]4)=[CH:7][CH:6]=[CH:5][C:4]=5[N:3]=3)[CH2:22][CH2:21]2)[CH2:13][CH2:8][CH2:9][CH2:10][CH2:11]1

Participants

5

Reactant 3

HCID 79372,6-LutidineHCID 522689Potassium FluorideHCID 11344780HCID 11344780, compound

Product 1

HCID 22667816HCID 22667816, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
140 °C

Procedure

400 mg of 2-chloro-4,5-dihydro-6H-imidazo[4,5,1-ij]quinolin-6-one in 5 mL of dimethylformamide, 70 mg of potassium fluoride, 0.2 mL of 2,6-lutidine and 1.6 g of 4-(N-methylpiperidinium)piperidine chloride are added to a three-necked flask under argon and left stirring for 5 hours at 140° C. The mixture is evaporated on a vacuum pump and the residue obtained is chromatographed with 70 g of Silica H (Merck) (eluent: dichloromethane with 10% methanol and 0.5% triethylamine). 50 mg of pure product are obtained, the NMR spectrum of which corresponds to the desired structure.

Workup

  1. waitleft
  2. customThe mixture is evaporated on a vacuum pump
  3. customthe residue obtained
  4. customis chromatographed with 70 g of Silica H (Merck) (eluent: dichloromethane with 10% methanol and 0.5% triethylamine)

Sources & evidence

ORD record
ord-d6feb179a2044811962e674c903d67b0
Source dataset
uspto-grants-2004_09
Patent number
US06794382B2

Reaction notes

Loading…