Pyridine → N-(6-methoxypyridin-3-yl)cyclopropanecarboxamide

HRID 373942Notes

Reaction equation

HRID 373942 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([O:8][CH3:9])=[N:6][CH:7]=1.N1C=CC=CC=1.[CH:16]1([C:19](Cl)=[O:20])[CH2:18][CH2:17]1.[OH-].[Na+]>ClCCl.O>[CH3:9][O:8][C:5]1[CH:4]=[CH:3][C:2]([NH:1][C:19]([CH:16]2[CH2:18][CH2:17]2)=[O:20])=[CH:7][N:6]=1

Participants

7

Reactant 4

HCID 1049PyridineHCID 14798Sodium HydroxideHCID 77637Cyclopropanecarbonyl chlorideHCID 811216-Methoxy-3-pyridinylamine

Product 1

HCID 86308N-(6-methoxypyridin-3-yl)cyclopropanecarboxamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

5-Amino-2-methoxy pyridine (12.4 g, 0.10 mol) and pyridine (10 ml) were mixed together in dichloromethane (200 ml) in a reaction flask. Cyclopropane carboxylic acid chloride (9.1 ml, 0.10 mol) was added to the reaction mixture over a period of 2 minutes. The reaction was exothermic and the temperature rose to 34° C. The reaction was allowed to stand for one hour at room temperature, after which the reaction mixture was wsahed with 5% sodium hydroxide (200 ml) and water (100 ml). The resulting organic phase was separated and dried over anhydrous magnesium sulfate. Crystals formed, so the mixture was filtered and washed with 300 ml of acetone and the filtrate evaporated in vacuo to give a solid that was triturated with hexane to yield 16.7 g, after drying. The product was identified by infrared (IR) and nuclear magnetic spectroscopy (NMR) analysis as the title compound, having a melting pont of 130°-131° C.

Workup

  1. customrose to 34° C
  2. customThe resulting organic phase was separated
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customCrystals formed, so the mixture
  5. filtrationwas filtered
  6. washwashed with 300 ml of acetone
  7. customthe filtrate evaporated in vacuo
  8. customto give a solid
  9. customthat was triturated with hexane
  10. customto yield 16.7 g
  11. customafter drying
  12. customa melting pont of 130°-131° C.

Sources & evidence

ORD record
ord-2b11a460bd3f4319bb59490f283d8137
Source dataset
uspto-grants-1992_11
Patent number
US05166215

Reaction notes

Loading…