ChemicalBook CAS DataBase List 5-METHOXY-PYRIDIN-2-YLAMINE

5-METHOXY-PYRIDIN-2-YLAMINE synthesis

11synthesis methods

Product Name:5-METHOXY-PYRIDIN-2-YLAMINE
CAS Number:10167-97-2
Molecular formula:C6H8N2O
Molecular Weight:124.14

76066-07-4

10167-97-2

General procedure for the synthesis of 2-amino-5-methoxypyridine from 2-bromo-3-methoxy-6-nitropyridine: 2-bromo-3-methoxy-6-nitropyridine (1.20 g, 5.15 mmol), hydrazine hydrate (6 mL), Pd/C (10%, 400 mg), and ethanol (40 mL) were mixed and heated to reflux for 45 minutes. Upon completion of the reaction, the mixture was allowed to cool and filtered through Celite. The filtrate was concentrated, water (20 mL) and saturated ammonia (10 mL) were added and extracted with chloroform (2 x 50 mL). The organic phases were combined, dried over anhydrous sodium sulfate and concentrated to give 2-amino-5-methoxypyridine as a colorless solid with a low melting point. Yield: 615 mg (96%).1H NMR (DMSO-d6, 400MHz) δ 7.64 (dd, 1H), 7.10 (dd, 1H), 6.42 (dd, 1H), 5.43 (br.s, 2H), 3.68 (s, 3H).

5-METHOXY-2-(2,5-DIMETHYL-1H-PYRROL-1-YL)PYRIDINE

638352-78-0
23 suppliers
$400.00/1g

10167-97-2
233 suppliers
$18.00/1g

Yield:10167-97-2 100%

Reaction Conditions:

with hydroxylamine hydrochloride;triethylamine in ethanol;water; for 20 h;Heating / reflux;

Steps:

20.C

A mixture of 118 (1.0 equiv., 257 mmol, 52.0 g), hydroxylamine hydrochloride(6.5 equiv., 1671 mmol, 69.5 g), triethylamine (2.0 equiv., 514 mmol, 52.0 g), ethanol(400 ml) and water (200 ml) was refiuxed for 20 h. The solution was cooled and quenched with 2 M HCl, washed with isopropyl ether and the pH was adjusted to 9-10 with 6 M NaOH. The resulting mixture was extracted several times with dichloro- methane. The combined organic phases were dried with MgSO₄ and the solvent was removed in vacuo. The oily residue was purified by column chromatography on silica gel (gradient elution: dichloromethane / ethyl acetate 25:75 -> ethyl acetate) to give 2-amino-5-methoxy-pyridine (119) (32.0 g, yield = 100 %). ¹U NMR (δ, CDCl₃): 3.74 (3H, s), 4.45 (2H, s {br) 6.45 (IH, d, J = 8.8 Hz), 7.07 (IH, dd, J = 8.8, 3.3 Hz), 7.72 (IH, d, J = 3.3 Hz)

References:

WO2007/113290,2007,A1 Location in patent:Page/Page column 40-42

76066-07-4 Synthesis

76066-07-4
102 suppliers
$44.00/250mg

10167-97-2
233 suppliers
$18.00/1g

References

1072-97-5 Synthesis