Methanol → 5-Bromo-6-methoxy-3-pyridinecarboxylic acid

HRID 1918312Notes

Reaction equation

HRID 1918312 reaction equation
C[O:2][C:3](=[O:13])[C:4]1[CH:9]=[C:8]([Br:10])[C:7]([O:11][CH3:12])=[N:6][CH:5]=1.[OH-].[Li+].CO>O1CCOCC1.O>[Br:10][C:8]1[C:7]([O:11][CH3:12])=[N:6][CH:5]=[C:4]([CH:9]=1)[C:3]([OH:13])=[O:2]

Participants

6

Reactant 3

HCID 887MethanolHCID 3939Lithium HydroxideHCID 46311221Methyl 5-bromo-6-methoxypyridine-3-carboxylate

Product 1

HCID 457904665-Bromo-6-methoxy-3-pyridinecarboxylic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
60 °C

Procedure

5-Bromo-6-methoxy-nicotinic acid methyl ester (W. J. Thompson et al., J. Org. Chem. 49 (1984), 5237-5243; 2.00 g, 8.13 mmol) was dissolved in dioxane (40 ml), lithium hydroxide (40 ml of a 1 M solution in water) was added and subsequently sufficient methanol to achieve complete dissolution. The mixture was stirred at 60° C. for 2 h.

Workup

  1. dissolutiondissolution

Sources & evidence

ORD record
ord-97baeb2699174942a3eed506997b79bf
Source dataset
uspto-grants-2013_12
Patent number
US08618304B2

Reaction notes

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