Sodium Carbonate → 4-[2-(2-Methoxynicotinamido)-ethyl]pyridine

HRID 1730288Notes

Reaction equation

HRID 1730288 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][N:7]=[CH:6][CH:5]=1.[C:10](=[O:13])([O-])[O-].[Na+].[Na+].[CH3:16][O:17][C:18]1[N:25]=[CH:24][CH:23]=[CH:22][C:19]=1CCl>O.C(Cl)Cl>[CH3:16][O:17][C:18]1[N:25]=[CH:24][CH:23]=[CH:22][C:19]=1[C:10]([NH:1][CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][N:7]=[CH:6][CH:5]=1)=[O:13]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 832754-PyridineethanamineHCID 149329453-(Chloromethyl)-2-methoxypyridine

Product 1

HCID 124252384-[2-(2-Methoxynicotinamido)-ethyl]pyridine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

A 3 liter, three neck, round bottom flask equipped with a mechanical stirrer, reflux condenser and dropping funnel was charged with 4-(2-aminoethyl)pyridine (61.0 g., 0.5 mole) in 50 ml. of methylene chloride. Sodium carbonate (124.0 g., 1.0 mole) in water was added in one portion, and with stirring the heterogeneous reaction mixture was cooled in an ice-bath. 2-Methoxynicotinyl chloride (86 g., 0.5 mole) in methylenechloride (500 ml.) was added drop-wise and the mixture was allowed to warm to room temperature as vigorous stirring was continued for 2 hours. At this point the organic layer was removed and the aqueous layer extracted twice with 100 ml. portions of methylene chloride. The combined organic layers were then extracted three times with cold, dilute (0.5N) sodium hydroxide. The organic layer was dried over sodium sulfate, filtered and concentrated in vacuo to a yellow oil, which solidified upon standing, affording 97 g. (0.37 mmole, 75%) of product. Recrystallization from cyclohexane gave the analytical sample, a white crystalline solid, m.p. 84°-97°.

Workup

  1. customA 3 liter, three neck, round bottom flask equipped with a mechanical stirrer
  2. temperaturereflux condenser
  3. temperaturewas cooled in an ice-bath
  4. stirringas vigorous stirring
  5. customAt this point the organic layer was removed
  6. extractionthe aqueous layer extracted twice with 100 ml
  7. extractionThe combined organic layers were then extracted three times with cold,
  8. additiondilute (0.5N) sodium hydroxide
  9. dry with materialThe organic layer was dried over sodium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated in vacuo to a yellow oil, which
  12. customaffording 97 g
  13. customRecrystallization from cyclohexane
  14. customgave the analytical sample

Sources & evidence

ORD record
ord-d5160a2d81284fe7a4f8c0f48dee3c98
Source dataset
uspto-grants-1976_11
Patent number
US03992388

Reaction notes

Loading…