ChemicalBook CAS DataBase List METHYL 5-BROMO-6-HYDROXYNICOTINATE

METHYL 5-BROMO-6-HYDROXYNICOTINATE synthesis

5synthesis methods

Product Name:METHYL 5-BROMO-6-HYDROXYNICOTINATE
CAS Number:381247-99-0
Molecular formula:C7H6BrNO3
Molecular Weight:232.03

66171-50-4 Synthesis

METHYL 6-OXO-1,6-DIHYDRO-3-PYRIDINECARBOXYLATE

66171-50-4
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381247-99-0
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$17.00/250mg

Yield:381247-99-0 100%

Reaction Conditions:

Stage #1: methyl 6-hydroxynicotinatewith bromine;acetic acid at 60;
Stage #2: with sodium hydrogencarbonate;sodium hydroxide at 18 - 26; pH=~ 7;

Steps:

117

Intermediate 117Methyl 5-bromo-6-hvdroxynicotininate Methyl 6-hydroxynicotininate (Intermediate 116, 50 g, 327 mmol) was suspended in acetic acid (250 mL) and bromine (26.2 mL, 490.5 mmol) was added dropwise to the reaction. The reaction was then heated at 6O⁰C for 18 h. The reaction mixture was cooled to room temperature, and saturated sodium thiosulfate solution was added to remove remaining bromine. Saturated sodium bicarbonate solution (500 mL) was added slowly, then IN sodium hydroxide was added carefully until the pH was ~7. The solid that precipitated were collected by filtration and dried in a vacuum oven at 50°C for 18 h. This gave 76g (100%) of methyl 5- bromo-6-hydroxynicotininate as an off white solid. MS (ESP): 231.9(MH⁺) for C₇H₆BrNO₃ ¹H NMR (300 MHz, DMSO-d₆): 3.80 (s, 3H), 8.12 (s, 1 H), 8.19 (s, IH), 12.77 (bs, IH).

References:

WO2009/106885,2009,A1 Location in patent:Page/Page column 296-297

67-56-1 Synthesis