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

HRID 2051465Notes

Reaction equation

HRID 2051465 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 grams, 0.10 mole) and 10 milliliters (ml) of pyridine were mixed together in 200 ml dichloromethane in a reaction flask. 9.1 ml (0.10 mole) of cyclopropane carboxylic acid chloride was added to the reaction mixture over a period of 2 minutes. The reaction was exothermic and temperature rose to 34° C. The reaction was allowed to stand for one hour at room temperature, after which the reaction mixture was added with 200 ml of 5% sodium hydroxide and 100 ml of water. 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 grams, after drying. The product was identified by IR and NMR as the title compound, having a melting point of 130°-131° C. This compound will be referred to as Compound 1.

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 grams
  11. customafter drying

Sources & evidence

ORD record
ord-7106d870279b4ce48559891b59498da5
Source dataset
uspto-grants-1991_05
Patent number
US05019565

Reaction notes

Loading…