Triethylamine → HCID 15617221, compound

HRID 1709408Notes

Reaction equation

HRID 1709408 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[C:4]([Cl:11])[N:3]=1.Cl.[CH2:13]([O:15][C:16](=[O:19])[CH2:17][NH2:18])[CH3:14].C(N(CC)CC)C>C(O)C>[CH2:13]([O:15][C:16](=[O:19])[CH2:17][NH:18][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[C:4]([Cl:11])[N:3]=1)[CH3:14]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 852392,6-Dichloro-3-nitropyridineHCID 2723640Glycine ethyl ester, hydrochloride

Product 1

HCID 15617221HCID 15617221, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a suspension of 2,6-dichloro-3-nitropyridine (1.0 g, 0.00518 mole) and glycine ethyl ester hydrochloride (0.725 g, 0.00518 mole) in absolute ethanol (10 ml) was added triethylamine (1.05 g, 0.0104 mole). The resulting solution was stirred overnight at room temperature under nitrogen. An additional portion of absolute ethanol (10 ml) was added and the suspension was filtered and the solid was washed with 3-10 ml portions of absolute ethanol. The combined filtrate and washings were evaporated under reduced pressure at room temperature to give a yellow solid which was triturated in water (30 ml) collected by filtration, and rinsed with additional water. The solid was recrystallized from isopropyl ether/light petroleum ether, and the resulting solid was purified by column chromatography (10 g of silica gel) with 1:1 isopropyl ether/light petroleum ether as the eluting solvent. The appropriate fraction was recrystallized from isopropyl ether and dried under high vacuum to give the title compound, mp 77.5°-80° C.

Workup

  1. filtrationthe suspension was filtered
  2. washthe solid was washed with 3-10 ml portions of absolute ethanol
  3. customThe combined filtrate and washings were evaporated under reduced pressure at room temperature
  4. customto give a yellow solid which
  5. customwas triturated in water (30 ml)
  6. filtrationcollected by filtration
  7. washrinsed with additional water
  8. customThe solid was recrystallized from isopropyl ether/light petroleum ether
  9. customthe resulting solid was purified by column chromatography (10 g of silica gel) with 1:1 isopropyl ether/light petroleum ether as the eluting solvent
  10. customThe appropriate fraction was recrystallized from isopropyl ether
  11. customdried under high vacuum

Sources & evidence

ORD record
ord-3ead3022eda3405d9afd56297a7a7bcf
Source dataset
uspto-grants-1990_08
Patent number
US04948800

Reaction notes

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