Hydrochloric Acid → HCID 23287782, compound

HRID 367031Notes

Reaction equation

HRID 367031 reaction equation
C([O:4][C:5]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[C:11]2[C:6]=1[CH2:7][CH2:8][C:9](=[O:17])[NH:10]2)(=O)C.[CH3:18][NH:19][CH3:20].[CH2:21]=O.[ClH:23]>C(O)C>[ClH:23].[CH3:18][N:19]([CH2:21][C:14]1[C:5]([OH:4])=[C:6]2[C:11](=[C:12]([O:15][CH3:16])[CH:13]=1)[NH:10][C:9](=[O:17])[CH2:8][CH2:7]2)[CH3:20]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 674DimethylamineHCID 712FormaldehydeHCID 11096556HCID 11096556, compound

Product 1

HCID 23287782HCID 23287782, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

1.5 Grams of 5-acetoxy-3,4-dihydro-8-methoxy-2(1H)-quinolinone was suspended in 10 ml of ethanol, to this suspension were added 4 ml of 50%-dimethylamine aqueous solution and 2 ml of 37%-formalin, this mixture was refluxed by heating for 10 hours. The reaction mixture was concentrated to dryness under reduced pressure, the residue was purified by a silica gel flash column chromatography (eluent: methylene chloride: methanol=20:1→10:1). The oily product thus obtained was dissolved in ethanol, this solution was acidified by adding hydrochloric acid, concentrated to dryness, and recrystallized from ethanol, there was obtained 3.8 g of 6-(dimethylaminomethyl)-3,4-dihydro-5-hydroxy-8-methoxy-2(1H)-quinolinone hydrochloride as white powdery product.

Workup

  1. temperaturethis mixture was refluxed
  2. temperatureby heating for 10 hours
  3. concentrationThe reaction mixture was concentrated to dryness under reduced pressure
  4. customthe residue was purified by a silica gel flash column chromatography (eluent: methylene chloride: methanol=20:1→10:1)
  5. customThe oily product thus obtained
  6. concentrationconcentrated to dryness
  7. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-8501457bda9344638d26d2673a9fba84
Source dataset
uspto-grants-2000_10
Patent number
US06133264

Reaction notes

Loading…