HCID 57754684, compound → HCID 57754593, compound

HRID 227090Notes

Reaction equation

HRID 227090 reaction equation
COC1C=CC(C[N:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11](=[O:18])[C:10]([C:19]([C:21]3[CH:22]=[N:23][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:25][CH:26]=3)=[O:20])=[CH:9]2)=CC=1>Cl.O1CCOCC1>[F:30][C:27]([F:28])([F:29])[C:24]1[N:23]=[CH:22][C:21]([C:19]([C:10]2[C:11](=[O:18])[C:12]3[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=3)[NH:8][CH:9]=2)=[O:20])=[CH:26][CH:25]=1

Participants

4

Reactant 1

HCID 57754684HCID 57754684, compound

Product 1

HCID 57754593HCID 57754593, compoundYield 58.4%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

800 mg (1.83 mmol) of 1-(4-methoxy-benzyl)-3-(6-trifluoromethyl-pyridine-3-carbonyl)-1H-quinolin-4-one was heated in a sealed tube to 120° C. in 15 mL of 4 M HCl in dioxane for 20 h. The solution was evaporated and the residue ultrasonicated in 20 mL saturated aqueous NaHCO3. Filtration of the solid followed by aqueous wash, DCM wash and drying gave 340 mg of a light-brown powder. LC-MSD, m/z for C16H9F3N2O2 [M+H]+=319.0; HPLC retention time: 1.8 min.

Workup

  1. customThe solution was evaporated
  2. customthe residue ultrasonicated in 20 mL saturated aqueous NaHCO3
  3. filtrationFiltration of the solid
  4. washwash
  5. customdrying

Sources & evidence

ORD record
ord-0b7c4b5d61f44acfa95e1abb99f75d07
Source dataset
uspto-grants-2009_07
Patent number
US07557213B2

Reaction notes

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