Triethylamine → HCID 14390509, compound

HRID 2072918Notes

Reaction equation

HRID 2072918 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1.Cl.[CH2:12]([O:14][C:15](=[O:19])[CH2:16][CH2:17][NH2:18])[CH3:13].C(N(CC)CC)C>C(O)C>[CH2:12]([O:14][C:15](=[O:19])[CH2:16][CH2:17][NH:18][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1)[CH3:13]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 796132-Chloro-3-nitropyridineHCID 458475beta-Alanine, ethyl ester, hydrochloride

Product 1

HCID 14390509HCID 14390509, compoundYield 109.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-chloro-3-nitropyridine (68.6 g, 0.434 mole), β-alanine ethyl ester hydrochloride (100 g, 0.651 mole), triethylamine (103.7 g, 1.03 mole) and 95% ethanol (675 ml) was refluxed for 5 hr and then stirred at room temperature overnight. The solvent was evaporated at reduced pressure and the residue was triturated in ethyl acetate (700 ml). The solid was filtered and washed with ethyl acetate. The filtrate was washed three times with water, dried over anhydrous sodium sulfate, filtered and evaporated at reduced pressure to give 113.4 g of an oil. The oil was eluted through a silica gel column (400 g) with ethyl acetate. The eluent was evaporated at reduced pressure to give 106.2 g of an oil (100% yield). A small portion of the oil was crystallized from petroleum ether to give 0.7 g of yellow solid of the title compound, mp. 32.5°-33.5° C.

Workup

  1. temperaturewas refluxed for 5 hr
  2. customThe solvent was evaporated at reduced pressure
  3. customthe residue was triturated in ethyl acetate (700 ml)
  4. filtrationThe solid was filtered
  5. washwashed with ethyl acetate
  6. washThe filtrate was washed three times with water
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. customevaporated at reduced pressure

Sources & evidence

ORD record
ord-77f5e80a5a9148e0acd406a6c24c9639
Source dataset
uspto-grants-1990_04
Patent number
US04914109

Reaction notes

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