Hydrochloric Acid → HCID 57754654, compound

HRID 227020Notes

Reaction equation

HRID 227020 reaction equation
Cl.COC1C=CC(C[N:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12](=[O:19])[C:11]([C:20]([C:22]3[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][N:23]=3)=[O:21])=[CH:10]2)=CC=1>O1CCOCC1>[CH3:28][C:25]1[CH:26]=[CH:27][C:22]([C:20]([C:11]2[C:12](=[O:19])[C:13]3[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=3)[NH:9][CH:10]=2)=[O:21])=[N:23][CH:24]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 57754554HCID 57754554, compound

Product 1

HCID 57754654HCID 57754654, compoundYield 26.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
120 °C

Procedure

A 4M solution of hydrochloric acid in dioxane (4 mL) was added to 381 mg (0.991 mmol) of 1-(4-Methoxy-benzyl)-3-(5-methyl-pyridine-2-carbonyl)-1H-quinolin-4-one and was heated in a pressure tube at 120° C. for 18 h. The reaction was concentrated and saturated sodium bicarbonate was added and the aqueous phase was extracted with dichloromethane (3×20 mL). The crude product was purified by flash column chromatography using a gradient of 70:30 ethyl acetate/methanol to afford 68.4 mg of 3-(5-Methyl-pyridine-2-carbonyl)-1H-quinolin-4-one.

Workup

  1. concentrationThe reaction was concentrated
  2. additionsaturated sodium bicarbonate was added
  3. extractionthe aqueous phase was extracted with dichloromethane (3×20 mL)
  4. customThe crude product was purified by flash column chromatography

Sources & evidence

ORD record
ord-8dea64cbae5b4f1cac31c015ab7cc84e
Source dataset
uspto-grants-2009_07
Patent number
US07557213B2

Reaction notes

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