Diethyl Ether → HCID 18957130, compound

HRID 2379428Notes

Reaction equation

HRID 2379428 reaction equation
Cl[C:2]1[C:11]2[C:6](=[C:7]([O:12][CH3:13])[CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][C:3]=1[C:14](=[O:22])[CH2:15][CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18].[CH2:23]([NH2:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C(OCC)C>O1CCCC1>[CH2:23]([NH:30][C:2]1[C:11]2[C:6](=[C:7]([O:12][CH3:13])[CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][C:3]=1[C:14](=[O:22])[CH2:15][CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 7504BenzylamineHCID 14956373HCID 14956373, compound

Product 1

HCID 18957130HCID 18957130, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

In a flame-dried, three-necked round-bottomed reaction flask equipped with reflux condenser, magnetic stirring bar and rubber septum, there were placed 3.0 g (0.0093 mole) of 4-chloro-3-(3-ethoxycarbonylpropionyl)-8-methoxyquinoline (the product of Preparation C) dissolved in 30 mL of dry tetrahydrofuran. Stirring was commenced and to the resulting ethereal solution were then added with 2.0 g (0.0186 mole) of benzylamine (available from the Eastman Kodak Company of Rochester, N.Y.), which was added over a five-minute period at room temperature (ca. 20° C.). The well-stirred reaction mixture was then heated to 60° C. and thereafter kept at that temperature for a period of six hours. Upon completion of this step (as revealed by thin layer chromatography (TLC) analysis), the final reaction mixture was filtered to remove precipitated benzylamine hydrochloride and the filtrate was subsequently evaporated to near dryness while under reduced pressure to afford a solid material as the residue. Trituration of the latter material with diethyl ether then gave 880 mg (22%) of essentially pure 4-benzylamino-3-(3-ethoxycarbonylpropionyl)-8-methoxyquinoline as the free base compound: mass spectrum, m/e 392; NMR (CDCL3) consistent with product. The latter batch of material was next dissolved in dry benzene and thereafter treated with anhydrous hydrogen chloride gas to ultimately yield 320 mg (8%) of pure 4-benzylamino-3-(3-ethoxycarbonylpropionyl)-8-methoxyquinoline as the hydrochloride salt (in the form of a monohydrate), m.p. 201°- 202° C. after one recrystallization from methanol-diethyl ether. The pure product was further characterized by means of mass spectrum (MS) analysis, in addition to elemental analysis. Mass spectrum, m/e 392.

Workup

  1. customIn a flame-dried, three-necked round-bottomed reaction flask equipped
  2. temperaturewith reflux condenser, magnetic stirring bar
  3. customthe product of Preparation C)
  4. addition), which was added over a five-minute period at room temperature (ca. 20° C.)
  5. customThe well-stirred reaction mixture
  6. customUpon completion of this step (as revealed by thin layer chromatography (TLC) analysis), the final reaction mixture
  7. filtrationwas filtered
  8. customto remove
  9. customprecipitated benzylamine hydrochloride
  10. customthe filtrate was subsequently evaporated
  11. customto afford a solid material as the residue

Sources & evidence

ORD record
ord-79b90cf2110e430b8bfb0364053f3290
Source dataset
uspto-grants-1994_11
Patent number
US05362743

Reaction notes

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