Methanol → 4-Bromo-6-(methoxycarbonyl)pyridine-2-carboxylic acid

HRID 421982Notes

Reaction equation

HRID 421982 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[N:5]=[C:4]([C:12]([O:14]C)=[O:13])[CH:3]=1.[OH-].[K+].CO.C(Cl)Cl>C(OCC)C>[Br:1][C:2]1[CH:7]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[N:5]=[C:4]([C:12]([OH:14])=[O:13])[CH:3]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 6344DichloromethaneHCID 14797Potassium HydroxideHCID 11953411HCID 11953411, compound

Product 1

HCID 469414564-Bromo-6-(methoxycarbonyl)pyridine-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 6.09 g of dimethyl 4-bromopyridine-2,6-dicarboxylate, 1.08 g of potassium hydroxide, 200 ml of methanol and 20 ml of methylene chloride was stirred at room temperature for 3 hours, and 200 ml of diethylether was added thereto. The resulting white solid was filtered, and then washed with ether. The obtained white solid was dissolved in water, and then 12 ml of hydrochloric acid (2 M) was added thereto. The resulting mixture was extracted with chloroform. The organic layer was dried over anhydrous magnesium sulfate and filtered, and the filtrate was concentrated in vacuo to give the title compound.

Workup

  1. filtrationThe resulting white solid was filtered
  2. washwashed with ether
  3. dissolutionThe obtained white solid was dissolved in water
  4. addition12 ml of hydrochloric acid (2 M) was added
  5. extractionThe resulting mixture was extracted with chloroform
  6. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-7c1c99340a9344178cb952ddeb941d5c
Source dataset
uspto-grants-2012_01
Patent number
US08101621B2

Reaction notes

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