Water → HCID 15744973, compound

HRID 1648316Notes

Reaction equation

HRID 1648316 reaction equation
[CH2:1]([N:4]([C:8]([CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([O:26][CH3:27])[C:21]=1[N:28]([C:32](=[O:34])C)C(=O)C)(C(OCC)=O)C(OCC)=O)[CH2:5][CH2:6][CH3:7])[CH2:2][CH3:3].O>[O-]CC.[Na+].C(O)C>[CH2:5]([N:4]([CH2:1][CH2:2][CH3:3])[CH:8]1[CH2:19][C:20]2[C:21](=[C:22]([O:26][CH3:27])[CH:23]=[CH:24][CH:25]=2)[NH:28][C:32]1=[O:34])[CH2:6][CH3:7]

Participants

5

Reactant 2

HCID 962WaterHCID 15744972HCID 15744972, compound

Product 1

HCID 15744973HCID 15744973, compoundYield 90.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 2723922Sodium ethoxideSolvent

Procedure

Diethyl (dipropylamino){(2-(diacetylamino)-3-methoxyphenyl)methyl}propanedioate (6.34 g) was dissolved in sodium ethoxide in ethanol (150 mL of 1.4 M). After 20 min, the solution was heated under reflux for 15 hours; water was added to the reaction after 1 hour (1 mL), 3 hours (2 mL), 4 hours (5 mL) and 5 hours (15 mL). The solution was filtered to remove precipitated inorganic material and the solvents were removed trader reduced pressure, and the residue was partitioned between ethyl acetate and water. The oil obtained after evaporation of the ethyl acetate was chromatographed on silica gel to give 3.3 g of 3-(dipropylamino)-3, 4-dihydro-8-methoxy-2(1H)quinolinone. The product was crystallized from pentane to give 2.0 g of product, mp 50°°-54° C. Anal Calcd for C16H24N2O2 : C, 69.53; H, 8.75; N, 10.14. Found: C, 69.56; H, 8.98; N, 10.24.

Workup

  1. temperaturethe solution was heated
  2. temperatureunder reflux for 15 hours
  3. filtrationThe solution was filtered
  4. customto remove
  5. customprecipitated inorganic material
  6. customthe solvents were removed trader reduced pressure
  7. customthe residue was partitioned between ethyl acetate and water
  8. customThe oil obtained
  9. customafter evaporation of the ethyl acetate
  10. customwas chromatographed on silica gel

Sources & evidence

ORD record
ord-9768aaab7aa941b3a0ec4b2495ba0f00
Source dataset
uspto-grants-1995_07
Patent number
US05436240

Reaction notes

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