Sodium Carbonate → Ethyl 2-bromo-5-methylpyridine-3-carboxylate

HRID 848209Notes

Reaction equation

HRID 848209 reaction equation
C([C:3](=[CH:7][C:8]([CH3:13])=[CH:9][N:10]([CH3:12])C)[C:4]([O-:6])=[O:5])#N.[BrH:14].[C:15](O)(=O)[CH3:16].C([O-])([O-])=O.[Na+].[Na+]>C(O)(=O)C>[Br:14][C:12]1[N:10]=[CH:9][C:8]([CH3:13])=[CH:7][C:3]=1[C:4]([O:6][CH2:15][CH3:16])=[O:5]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 21893785Acetic Acid Mixture with Hydrobromic AcidHCID 86737883HCID 86737883, compound

Product 1

HCID 12919731Ethyl 2-bromo-5-methylpyridine-3-carboxylateYield 35%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

The crude 2-cyano-5-(N,N-dimethylamino)-4-methyl-2,4-pentanedienoate (15.9 g) was dissolved in acetic acid (50 ml) and the mixture heated at 40°. A solution of 30% HBr/acetic acid (100 ml) was added dropwise and then the mixture was heated to 55° with stirring. After heating for 3/4 of an hour, the solution was poured onto ice, neutralized with solid Na2CO3 and extracted with CH2Cl2 (4×200 ml). The organic extracts were dried over Na2SO4, filtered and concentrated to dryness. The residue was distilled at 114°-120° (0.4 mm) to yield 6.3 g (35% yield) of ethyl 2-bromo-5-methylnicotinate.

Workup

  1. temperaturethe mixture heated at 40°
  2. temperaturethe mixture was heated to 55°
  3. temperatureAfter heating for 3/4 of an hour
  4. additionthe solution was poured onto ice
  5. extractionextracted with CH2Cl2 (4×200 ml)
  6. dry with materialThe organic extracts were dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated to dryness
  9. distillationThe residue was distilled at 114°-120° (0.4 mm)

Sources & evidence

ORD record
ord-7f517f68b25c4b67ba2ff4d57dcb6e38
Source dataset
uspto-grants-1981_10
Patent number
US04294969

Reaction notes

Loading…