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

HRID 893073Notes

Reaction equation

HRID 893073 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>ClCCl>[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

5

Reactant 3

HCID 1049PyridineHCID 77637Cyclopropanecarbonyl chlorideHCID 811216-Methoxy-3-pyridinylamine

Product 1

HCID 86308N-(6-methoxypyridin-3-yl)cyclopropanecarboxamideYield 87%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 5-amino-2-methoxy pyridine (12.4 g, 0.10 mol) and pyridine (10 ml) in dichloromethane (200 ml) was stirred at room temperature. Cyclopropane carboxylic acid chloride (9.1 ml, 0.10 mol) was added dropwise to the reaction mixture at such a rate to maintain the temperature at 20°-30° C. After complete addition the reaction mixture was stirred at room temperature for a further one hour, then washed with 5% sodium hydroxide (200 ml), water (100 ml) and dried over anhydrous magnesium sulphate. Removal of the solvent gave N-(2-methoxy-5-pyridyl)-cyclopropane carboxamide (16.7 g, 87%) m.p. 130-131° C.

Workup

  1. temperatureto maintain the temperature at 20°-30° C
  2. additionAfter complete addition the reaction mixture
  3. washwashed with 5% sodium hydroxide (200 ml), water (100 ml)
  4. dry with materialdried over anhydrous magnesium sulphate
  5. customRemoval of the solvent

Sources & evidence

ORD record
ord-4c5052f0257f4724be95906086d979e2
Source dataset
uspto-grants-1992_06
Patent number
US05122529

Reaction notes

Loading…