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

HRID 1172424Notes

Reaction equation

HRID 1172424 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.ClCCl>CCOCC>[Br:1][C:2]1[CH:3]=[C:4]([C:12]([OH:14])=[O:13])[N:5]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[CH:7]=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 dichloromethane was stirred at room temperature for 3 hours, and 200 ml of ether 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-b5f159d62e1449aea3458e8af1c25883
Source dataset
uspto-grants-2010_11
Patent number
US07834018B2

Reaction notes

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