ChemicalBook CAS DataBase List 2-Phenylquinolin-4-ol

2-Phenylquinolin-4-ol synthesis

6synthesis methods

Product Name:2-Phenylquinolin-4-ol
CAS Number:1144-20-3
Molecular formula:C15H11NO
Molecular Weight:221.25

142-04-1
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$10.00/10g

94-02-0
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$14.00/5g

1144-20-3
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$60.00/100mg

Yield:-

Reaction Conditions:

with PPA;aniline in ammonium hydroxide;water;ethyl acetate;toluene

Steps:

1.B Synthesis of 2-phenyl-4-hydroxyquinoline (1b):
Example 1B Synthesis of 2-phenyl-4-hydroxyquinoline (1b): Commercially available ethyl benzoylacetate (6.00 g, 31.2 mmol) was heated at 85° C. (sealed tube) in 75 mL of 30% NH₄OH for 2 hours. The solid formed upon cooling was filtered and refluxed in water for 2 hours. The solution was extracted three times with CH₂Cl₂. The organic layers were combined, dried over MgSO₄, filtered and concentrated. The yellow residue was flash chromatographed on silica gel, eluding with EtOAc:hexane (3:7), to give the corresponding amide as a white solid, 1.60 g, 31% yield. This amide (250 mg, 1.53 mmol) was refluxed using a Dean-Stark apparatus with aniline (143 mg, 1.53 mmol) and aniline.HCl (10 mg, 0.08 mmol) in toluene (10 mL) for 16 h. The solution was concentrated to afford a brown oil that was mixed with polyphosphoric acid (2 g) and heated at 135° C. for 20 min. The reaction mixture was poured into water and adjusted to pH 8 with 5 M NaOH. The aqueous suspension was extracted twice with ethyl acetate. The organic layers were combined, washed with brine, dried over MgSO₄, filtered and concentrated. The residue was flash chromatographed on silica gel, eluding with 3% MeOH in ethyl acetate, to give 2-phenyl-4-hydroxyquinoline (2), 67 mg, 20% yield. ¹H NMR (DMSO-d₆) δ 8.11 (d, J=7 Hz, 1H), 7.86-7.83 (m, 2H), 7.77 (d, J=8 Hz, 1H), 7.68 (dd, J=8, 7 Hz, 1H), 7.61-7.58 (m, 3H), 7.35 (dd, J=8, 7 Hz, 1H), 6.34 (s, 1H).

References:

Boehringer Ingelheim (Canada) Ltd. US6767991, 2004, B1

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