ChemicalBook CAS DataBase List 2-PHENYL-ISONICOTINIC ACID

2-PHENYL-ISONICOTINIC ACID synthesis

8synthesis methods

Product Name:2-PHENYL-ISONICOTINIC ACID
CAS Number:55240-51-2
Molecular formula:C12H9NO2
Molecular Weight:199.21

66572-56-3

98-80-6

55240-51-2

Under nitrogen protection, 2-bromo-4-pyridinecarboxylic acid (0.210 g, 1.040 mmol) was dissolved in degassed 1,2-dimethoxyethane (DME, 8 mL). Tetrakis(triphenylphosphine)palladium(0) (0.060 g, 0.052 mmol) was added to the solution and the reaction mixture was stirred for 15 minutes. Subsequently, aqueous potassium carbonate (4.16 mL, 8.32 mmol) and phenylboronic acid (0.171 g, 1.403 mmol) were added. The reaction mixture was refluxed at 95 °C for 18 h, after which it was cooled to room temperature. The reaction mixture was filtered through diatomaceous earth and the pH was adjusted to 3-4 with acid to precipitate a white precipitate, which was filtered and washed with water. The white powdery product 2-phenyl-pyridine-4-carboxylic acid was obtained by recrystallization from 2-methoxyethanol. Yield: 0.106 g, 57% yield. The product was characterized by 1H NMR (400 MHz, DMSO-d6): δ 7.44-7.60 (m, 3H), 7.71-7.86 (dd, J = 4.9, 1.5 Hz, 1H), 8.05-8.19 (m, 2H), 8.23-8.35 (t, J = 1.2 Hz, 1H), 8.79-8.93 (dd, J = 5.1, 0.8 Hz, 1H), 13.56-13.97 (s, 1H).UPLC-ESI analysis: retention time 1.37 min, m/z 200.5 [M + H]+ (purity 92%).

3475-21-6
118 suppliers
$45.00/2.5mg

55240-51-2
100 suppliers
$45.00/10mg

Yield:55240-51-2 84%

Reaction Conditions:

with selenium(IV) oxide in pyridineHeating / reflux;

Steps:

4
2-phenyl-4-methylpyridine (6 g, 35.4 mmol) and SeO₂ (24 g, 216 mmol) were refluxed in pyridine (100 ml) overnight under argon. The mixture was then filtered through celite while hot. The Celite filter cake was rinsed with pyridine (3x50 ml) and the resulting filtrate evaporated to dryness. The solid thus obtained was triturated in water (200 ml) and filtered off. The resulting brown solid was suspended in a mixture of water (150 ml) and MeOH (200 ml) and made basic by addition of an aqueous NaOH solution. The mixture was then filtered over Celite to removed some insoluble materials. The filtrate was then acidified with concentrated HCl. MeOH was evaporated and the formed precipitate was filtered, washed with water, then small portions Of Et₂O (3x20 ml) and finally dried to afford 5.9 g (84%) of the titled compound as a slightly brown solid.

References:

KONINKLIJKE PHILIPS ELECTRONICS N.V. WO2007/4113, 2007, A2 Location in patent:Page/Page column 24

FullText

66572-56-3 Synthesis

66572-56-3
351 suppliers
$7.00/5g

98-80-6 Synthesis

98-80-6
738 suppliers
$5.00/5g

55240-51-2
100 suppliers
$45.00/10mg

References