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

HRID 1475723Notes

Reaction equation

HRID 1475723 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. The methanol was evaporated in vacuo and the remaining mixture was acidified with 2 N hydrochloric acid and extracted with EA. The combined extracts were dried over sodium sulfate, filtered and evaporated to dryness to yield the title compound.

Workup

  1. dissolutiondissolution
  2. customThe methanol was evaporated in vacuo
  3. extractionextracted with EA
  4. dry with materialThe combined extracts were dried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-55992b6fb1d943c5ac0348aed49c4555
Source dataset
uspto-grants-2015_04
Patent number
US09018383B2

Reaction notes

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