2-Methylbenzylamine → HCID 18957127, compound

HRID 2379429Notes

Reaction equation

HRID 2379429 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].[CH3:23][C:24]1[CH:31]=[CH:30][CH:29]=[CH:28][C:25]=1[CH2:26][NH2:27]>O1CCCC1>[CH2:20]([O:19][C:17]([CH2:16][CH2:15][C:14]([C:3]1[CH:4]=[N:5][C:6]2[C:11]([C:2]=1[NH:27][CH2:26][C:25]1[CH:28]=[CH:29][CH:30]=[CH:31][C:24]=1[CH3:23])=[CH:10][CH:9]=[CH:8][C:7]=2[O:12][CH3:13])=[O:22])=[O:18])[CH3:21]

Participants

4

Reactant 2

HCID 69932-MethylbenzylamineHCID 14956373HCID 14956373, compound

Product 1

HCID 18957127HCID 18957127, 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 was placed 1.0 g (0.0031 mole) of 4-chloro-3-(3-ethoxycarbonylpropionyl)-8-methoxyquinoline (the product of Preparation C) dissolved in 10 mL of dry tetrahydrofuran. Stirring was commenced and 0.8 mL (750 mg, 0.0062 mole) of 2-methylbenzylamine (available from the Aldrich Chemical Company, Inc. of Milwaukee, Wis.), was added over a two-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 approximately 16 hours (i.e., overnight). Upon completion of this step, the resulting reaction mixture was then filtered to remove 2-methylbenzylamine hydrochloride that had precipitated from the mixture and the filtrate was subsequently evaporated to near dryness while under reduced pressure to afford a crude solid product as the residue. The latter material was then purified by means of column chromatography over silica gel, using a 1% solution of diethylamine in ethyl acetate as the eluant. In this manner, there was ultimately obtained a 43 mg (3%) yield of pure 3-(3-ethoxycarbonylpropionyl)-8-methoxy-4-(2-methylbenzylamino)quinoline as the free base compound (isolated as a 0.25 hydrate), m.p. 152°-155° C. The pure product was further characterized by means of mass spectrum (MS) analysis and nuclear magnetic resonance (NMR) data, in addition to elemental analysis.

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), was added over a two-minute period at room temperature (ca. 20° C.)
  5. customThe well-stirred reaction mixture
  6. custom(i.e., overnight)
  7. customUpon completion of this step, the resulting reaction mixture
  8. filtrationwas then filtered
  9. customto remove 2-methylbenzylamine hydrochloride that
  10. customhad precipitated from the mixture
  11. customthe filtrate was subsequently evaporated
  12. customto afford a crude solid product as the residue
  13. customThe latter material was then purified by means of column chromatography over silica gel

Sources & evidence

ORD record
ord-8df90eb8f792423793c24a2423906775
Source dataset
uspto-grants-1994_11
Patent number
US05362743

Reaction notes

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