HCID 59355447, compound → HCID 59355425, compound

HRID 887729Notes

Reaction equation

HRID 887729 reaction equation
C[O:2][C:3]([C:5]1[C:10]([NH2:11])=[C:9]([Br:12])[CH:8]=[C:7]([Cl:13])[N:6]=1)=[O:4]>CO.[OH-].[Na+]>[NH2:11][C:10]1[C:5]([C:3]([OH:4])=[O:2])=[N:6][C:7]([Cl:13])=[CH:8][C:9]=1[Br:12]

Participants

4

Reactant 1

HCID 59355447HCID 59355447, compound

Product 1

HCID 59355425HCID 59355425, compoundYield 86.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
50 °C

Procedure

3-Amino-4-bromo-6-chloro-pyridine-2-carboxylic acid methyl ester (169 mg) was suspended in methanol (3 mL) and 2N sodium hydroxide solution (2 mL). The suspension was stirred at 50° C. for 3 hours. The precipitate was filtered off and washed carefully with diethyl ether. The precipitate was dissolved in a mixture of 2N hydrochloric acid and ethyl acetate and the layers were separated. The aqueous layer was 2× extracted with ethyl acetate, washed with brine, dried over MgSO4 and concentrated in vacuum to afford 138 mg of the title compound of the formula

Workup

  1. filtrationThe precipitate was filtered off
  2. washwashed carefully with diethyl ether
  3. dissolutionThe precipitate was dissolved in a mixture of 2N hydrochloric acid and ethyl acetate
  4. customthe layers were separated
  5. extractionextracted with ethyl acetate
  6. washwashed with brine
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated in vacuum

Sources & evidence

ORD record
ord-51ed3d2beb9943f2a612655966b30455
Source dataset
uspto-grants-2012_08
Patent number
US08247431B2

Reaction notes

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