Triethylamine → HCID 14390510, compound

HRID 2351595Notes

Reaction equation

HRID 2351595 reaction equation
[Cl:1][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>[ClH:1].[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 14390510HCID 14390510, compoundYield 3.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The mixture of 2-chloro-3-nitropyridine (25.8 g, 0.16 mole), β-alanine ethyl ester hydrochloride (50 g, 0.33 mole), triethylamine (49.4 g, 0.49 mole), and 300 ml of absolute ethanol was warmed at 50°-55° C. for 4 hr with mechanical stirring. The reaction mixture was evaporated and the residue was partitioned between water and methylene chloride. The water layer was separated and extracted with methylene chloride (2×). The combined methylene chloride extracts were washed with water (2×) and dried over anhydrous sodium sulfate. The filtrate was evaporated to an orange oil (39.2 g). A 2-g sample of the oil was dissolved in acetonitrile acidified with ethereal hydrogen chloride (excess), and scratched to initiate crystallization. The yellow solid was filtered off, washed with ether, and dried under high vacuum at room temperature overnight to give 1.62 g of the title compound, mp 137°-40° C. (sealed tube).

Workup

  1. temperaturewas warmed at 50°-55° C. for 4 hr with mechanical stirring
  2. customThe reaction mixture was evaporated
  3. customthe residue was partitioned between water and methylene chloride
  4. customThe water layer was separated
  5. extractionextracted with methylene chloride (2×)
  6. washThe combined methylene chloride extracts were washed with water (2×)
  7. dry with materialdried over anhydrous sodium sulfate
  8. customThe filtrate was evaporated to an orange oil (39.2 g)
  9. dissolutionA 2-g sample of the oil was dissolved in acetonitrile
  10. customcrystallization
  11. filtrationThe yellow solid was filtered off
  12. washwashed with ether
  13. customdried under high vacuum at room temperature overnight
  14. customto give

Sources & evidence

ORD record
ord-11aaa8a08f3a488bbbc4bb3a252618d0
Source dataset
uspto-grants-1989_10
Patent number
US04873251

Reaction notes

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