Triethylamine → N'-Ethyl-3-methyloxy-N',2-diphenyl-4-quinolinecarbohydrazide

HRID 1455517Notes

Reaction equation

HRID 1455517 reaction equation
[CH3:1][O:2][C:3]1[C:4]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[N:5][C:6]2[C:11]([C:12]=1[C:13](Cl)=[O:14])=[CH:10][CH:9]=[CH:8][CH:7]=2.CCN(CC)CC.[CH2:29]([N:31]([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[NH2:32])[CH3:30]>C(Cl)Cl>[CH2:29]([N:31]([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[NH:32][C:13]([C:12]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:3]=1[O:2][CH3:1])=[O:14])[CH3:30]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 695171-Ethyl-1-phenylhydrazineHCID 213546903-Methyloxy-2-phenyl-4-quinolinecarbonyl chloride

Product 1

HCID 10340761N'-Ethyl-3-methyloxy-N',2-diphenyl-4-quinolinecarbohydrazideYield 53%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

The 3-methyloxy-2-phenyl-4-quinolinecarbonyl chloride obtained in Step 1 was dissolved in CH2Cl2 (2 mL) and added dropwise to a solution of Et3N (104 μL, 0.76 mmol) and 1-ethyl-1-phenylhydrazine (102 mg, 0.76 mmol) [Synthesis 1983, 157-158] in CH2Cl2 (3 mL) at 0° C. After stirring at 0° C. for 2 h the cooling bath was removed and the solution stirred at room temperature for 18 h. The solvent was evaporated and the residue taken up in ethyl acetate (20 mL). The organic phase was washed with H2O (2×10 mL), 1N NaOH (20 mL) and brine (20 mL). The organic phase was separated, dried (MgSO4) and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel, eluting with isohexane:ethyl acetate (2:1). The fractions containing the desired product were combined, evaporated and triturated with diethyl ether. The title compound (159 mg, 53%) was isolated as a colourless solid. 1H NMR (CDCl3, 400 MHz), δ 8.09 (1H, d, J=7.6 Hz), 7.96-7.93 (2H, m), 7.70 (1H, d, J=7.6 Hz), 7.63 (1H, dt, J=7.0 and 1.4 Hz), 7.51-7.45 (6H, m), 7.42-7.28 (4H, m), 5.36-5.35 (1H, broad s), 4.21-4.19 (1H, m), 3.48 (3H, s). MS (ES+) C26H25N3O2 requires: 411, found: 412 (M+H+, 100%).

Workup

  1. customwas removed
  2. stirringthe solution stirred at room temperature for 18 h
  3. customThe solvent was evaporated
  4. washThe organic phase was washed with H2O (2×10 mL), 1N NaOH (20 mL) and brine (20 mL)
  5. customThe organic phase was separated
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by column chromatography on silica gel
  9. washeluting with isohexane:ethyl acetate (2:1)
  10. additionThe fractions containing the desired product
  11. customevaporated
  12. customtriturated with diethyl ether

Sources & evidence

ORD record
ord-fefc1d8514474630b8d70be6f28df5b8
Source dataset
uspto-grants-2009_01
Patent number
US07482457B2

Reaction notes

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