ChemicalBook CAS DataBase List 5-BROMO-1-METHYL-2(1H)-PYRIDINONE

5-BROMO-1-METHYL-2(1H)-PYRIDINONE synthesis

8synthesis methods

Product Name:5-BROMO-1-METHYL-2(1H)-PYRIDINONE
CAS Number:81971-39-3
Molecular formula:C6H6BrNO
Molecular Weight:188.02

13466-38-1

74-88-4

81971-39-3

5-Bromopyridin-2(1H)-one (8.6 g, 0.05 mol) was dissolved in THF (120 mL) at 0 °C and slowly added to a suspension of NaH (4.8 g, 0.2 mol) in THF (10 mL). The reaction mixture was stirred at 0 °C for 1 hour. Subsequently, iodomethane (35.5 g, 0.25 mol) was added dropwise to the mixture and stirring was continued for 3 hours at room temperature. After completion of the reaction, the reaction was quenched with saturated aqueous NH4Cl solution. The organic phase was separated and concentrated to give the crude product. The crude product was purified by column chromatography to afford 5-bromo-1-methylpyridin-2(1H)-one (8.9 g, 96.78% yield).1H NMR (CDCl3): δ= 3.5 (s, 3H), 6.52 (m, 1H), 7.32 (m, 1H), 7.45 (m, 1H).

13466-38-1 Synthesis

13466-38-1
406 suppliers
$6.00/5g

74-88-4
356 suppliers
$15.00/10g

81971-39-3
119 suppliers
$45.00/100mg

Yield:81971-39-3 96.78%

Reaction Conditions:

Stage #1: 5-bromopyridin-2(1H)-onewith sodium hydride in tetrahydrofuran at 0; for 1 h;
Stage #2: methyl iodide in tetrahydrofuran; for 3 h;

Steps:

30.1

To a suspension of NaH (4.8 g, 0.2 mol) in THF (10 mL) was added a solution of 5-bromopyridin-2(1H)-one (8.6 g, 0.05 mol) in THF (120 mL) at 0° C. The resulting mixture was stirred for 1 h and CH₃I (35.5 g, 0.25 mol) was added. The mixture was stirred for 3 h. The reaction was quenched with aqueous NH₄Cl solution. The organic phase was concentrated to give the crude product, which was purified by column chromatography to give 5-bromo-1-methylpyridin-2(1H)-one (8.9 g, 96.78%). ¹H NMR (CDCl₃): δ=3.5 (S, 3H), 6.52 (m, 1H), 7.32 (m, 1H), 7.45 (m, 1H).

References:

US2010/331320,2010,A1 Location in patent:Page/Page column 56

13466-38-1 Synthesis

13466-38-1
406 suppliers
$6.00/5g

74-88-4
356 suppliers
$15.00/10g

81971-39-3
119 suppliers
$45.00/100mg

References