2-Chloronicotinoyl chloride → N-(2-Bromo-6-methoxy-3-pyridinyl)-2-chloro-3-pyridinecarboxamide

HRID 53523

Reaction equation

HRID 53523 reaction equation
[NH2:1][C:2]1[C:3]([Br:10])=[N:4][C:5]([O:8][CH3:9])=[CH:6][CH:7]=1.[Cl:11][C:12]1[N:20]=[CH:19][CH:18]=[CH:17][C:13]=1[C:14](Cl)=[O:15]>C(Cl)Cl.N1C=CC=CC=1>[Br:10][C:3]1[C:2]([NH:1][C:14]([C:13]2[C:12]([Cl:11])=[N:20][CH:19]=[CH:18][CH:17]=2)=[O:15])=[CH:7][CH:6]=[C:5]([O:8][CH3:9])[N:4]=1

Participants

5

Reactant 2

HCID 27745412-Chloronicotinoyl chlorideHCID 152093242-Bromo-6-methoxypyridin-3-amine

Product 1

HCID 10617311N-(2-Bromo-6-methoxy-3-pyridinyl)-2-chloro-3-pyridinecarboxamideYield 95.7%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 3-amino-2-bromo-6-methoxypyridine (2.7 g) in methylene chloride (20 ml) and pyridine (1 ml) was added 2-chloronicotinoyl chloride (2.2 g), and the resulting mixture was stirred 20 min. The mixture was then diluted with methylene chloride (100 ml), washed with water (100 ml), dried (anhydrous magnesium sulfate), and concentrated. The semisolid residue was saturated with hexane, filtered, and dried to give 4.1 g of product suitable for use in the next reaction.

Workup

  1. washwashed with water (100 ml)
  2. dry with materialdried (anhydrous magnesium sulfate)
  3. concentrationconcentrated
  4. filtrationfiltered
  5. customdried

Sources & evidence

ORD record
ord-ab68f65f49af453c8471dd3e1e060b1a
Source dataset
uspto-grants-1997_04
Patent number
US05620974

Linked notes

Loading…