Triethylamine → Ethyl 5-methylpyridine-2-carboxylate

HRID 1650339

Reaction equation

HRID 1650339 reaction equation
[CH2:1](N(CC)CC)C.Br[CH:9]([CH2:15]Br)[C:10]([O:12][CH2:13][CH3:14])=[O:11].CN(C)[CH:19]=[CH:20][C:21]([NH2:23])=C>O1CCOCC1>[CH3:19][C:20]1[CH:1]=[CH:15][C:9]([C:10]([O:12][CH2:13][CH3:14])=[O:11])=[N:23][CH:21]=1

Participants

5

Reactant 3

HCID 8471Triethylamine2×HCID 97945Ethyl 2,3-dibromopropionateHCID 867439031-Dimethylamino-1-aza-3-methyl-1,3-butadiene

Product 1

HCID 12243769Ethyl 5-methylpyridine-2-carboxylate

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

6.1 g of triethylamine are added at 0° C. to 13 g of ethyl 2,3-di-bromopropionate in 50 ml of dioxane. The mixture is stirred for 2 hours at room temperature and then a solution of 5.6 g of 1-dimethylamino-1-aza-3-methyl-1,3-butadiene and 6.1 g of triethylamine in 50 ml of dioxane is added dropwise. The reaction mixture is kept for 30 hours at 70° C. and then cooled and concentrated by evaporation. The residue is partitioned between water and ether and the organic phase is washed with brine, dried and concentrated by evaporation. The residue is distilled under reduced pressure, affording 3.2 g of the title compound as an oil with a boiling point of 69°-74° C. (at 0.08 mbar).

Workup

  1. waitThe reaction mixture is kept for 30 hours at 70° C.
  2. temperaturecooled
  3. concentrationconcentrated by evaporation
  4. customThe residue is partitioned between water and ether
  5. washthe organic phase is washed with brine
  6. customdried
  7. concentrationconcentrated by evaporation
  8. distillationThe residue is distilled under reduced pressure

Sources & evidence

ORD record
ord-9a1d28c43bd94341a7846ecc45555c03
Source dataset
uspto-grants-1990_05
Patent number
US04923993

Linked notes

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