Carbon Tetrachloride → 2-(3-Methoxy-2-phenylquinolin-4-yl)-5-phenyl-5-propyl-2-oxazoline

HRID 2227457Notes

Reaction equation

HRID 2227457 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:20][O:21][C:22]1[C:23]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)=[N:24][C:25]2[C:30]([C:31]=1[C:32](O)=[O:33])=[CH:29][CH:28]=[CH:27][CH:26]=2.C(N(CC)CC)C.[NH2:48][CH2:49][C:50]([C:55]1[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=1)(O)[CH2:51][CH2:52][CH3:53].C(Cl)(Cl)(Cl)Cl>C(Cl)(Cl)Cl.C(#N)C.N1C=CC=CC=1>[CH3:20][O:21][C:22]1[C:23]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)=[N:24][C:25]2[C:30]([C:31]=1[C:32]1[O:33][C:50]([C:55]3[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=3)([CH2:51][CH2:52][CH3:53])[CH2:49][N:48]=1)=[CH:29][CH:28]=[CH:27][CH:26]=2

Participants

9

Reactant 5

HCID 5943Carbon TetrachlorideHCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 6243483-Methoxy-2-phenylquinoline-4-carboxylic acidHCID 229923231-Amino-2-phenylpentan-2-ol

Product 1

HCID 120436612-(3-Methoxy-2-phenylquinolin-4-yl)-5-phenyl-5-propyl-2-oxazolineYield 17.2%

Reagents, catalysts & solvents 3

HCID 1049PyridineSolventHCID 6212ChloroformSolventHCID 6342AcetonitrileSolvent

Procedure

Triphenylphosphine (2.10 g, 8.0 mmol) is added to a mixture of (3-methoxy-2-phenylquinolin-4-yl)carboxylic acid (0.61 g, 2.2 mmol), pyridine (anhydrous, 5 mL), acetonitrile (anhydrous, 5 mL), triethylamine (1.4 mL, 10 mmol), 1-amino-2-phenyl-2-pentanol (0.40 g, 2.2 mmol), and carbon tetrachloride (1.5 mL, 16 mmol) stirred under nitrogen at ambient temperature. After stirring for 1 h without heating, the mixture is stirred at 40° C. for 2 h. The reaction mixture is dissolved in chloroform (100 mL). The solution is washed with 10% acetic acid (100 mL) followed by 5% sodium bicarbonate (100 mL) and dried over sodium carbonate. The solvent is evaporated under reduced pressure. The crude product is subjected to column chromatography on silica gel using chloroform-diethyl ether (49:1) and then to preparative TLC using hexanes-diethyl ether (3:1) as an eluent to give the titled compound (160 mg, 17%). 1H NMR (CDCl3) δ0.93(t, J=7.5 Hz, 3 H), 1.32 (m, 1 H), 1.48 (m, 1 H), 2.13 (m, 2 H), 3.60 (s, 3 H), 4.35 (d, J=14.6 Hz, 1 H), 4.40 (d, J=14.6 Hz, 1 H), 7.31 (tt, J=7.1 and 1.5 Hz, 1 H), 7.40 (t, J=7.4 Hz, 2 H), 7.43-7.56 (m, 6 H), 7.67 (ddd, J=8.2, 6.9 and 1.5 Hz, 1 H) 7.96 (dd, J=8.4 and 1.5 Hz, 1 H), 8.07 (m, 2 H), 8.17 (d, J=8.5 Hz, 1 H). LC-MS data (same condition as given in example 1): HPLC: 2.62 min. MS (ES+): m/e 407 [MH]+.

Workup

  1. stirringAfter stirring for 1 h
  2. temperaturewithout heating
  3. stirringthe mixture is stirred at 40° C. for 2 h
  4. washThe solution is washed with 10% acetic acid (100 mL)
  5. dry with materialdried over sodium carbonate
  6. customThe solvent is evaporated under reduced pressure

Sources & evidence

ORD record
ord-e3012c038f014bfca7bde83e00485b12
Source dataset
uspto-grants-2002_07
Patent number
US06413982B1

Reaction notes

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