Anthranilamide → HCID 722983, compound

HRID 1648213Notes

Reaction equation

HRID 1648213 reaction equation
[C:1]([NH2:10])(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[NH2:4].C(N(CC)CC)C.Cl.[C:19](Cl)(=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[N:22][CH:21]=1>O1CCCC1.C(Cl)Cl>[N:22]1[CH:23]=[CH:24][CH:25]=[C:20]([C:19]([NH:4][C:3]2[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=2[C:1]([NH2:10])=[O:9])=[O:26])[CH:21]=1

Participants

5

Reactant 3

HCID 6942AnthranilamideHCID 8471TriethylamineHCID 884383-Pyridinecarbonyl chloride, hydrochloride (1:1)

Product 1

HCID 722983HCID 722983, compoundYield 79.1%

Reagents, catalysts & solvents 1

HCID 21919333Tetrahydrofurane dichloromethaneSolvent

Procedure

To a solution of anthranilamide (8.2 g, being on sale) and triethylamine (18.0 g)in 100 mL of tetrahydrofuran/methylene chloride (1:1), was added nicotinoyl chloride hydrochloride (10.8 g). The mixture was allowed to stir at room temperature, under nitrogen atmosphere, for six hours. The solution was then concentrated under reduced pressure. The concentrate was taken up in ethyl acetate and water and the mixture filtered. The solid material was triturated in ether and filtered to give the title compound (11.5 g) as a yellow powder having the following physical data.

Workup

  1. concentrationThe solution was then concentrated under reduced pressure
  2. filtrationwater and the mixture filtered
  3. customThe solid material was triturated in ether
  4. filtrationfiltered

Sources & evidence

ORD record
ord-43fef8841a4c4572974097215f443c08
Source dataset
uspto-grants-1995_07
Patent number
US05436233

Reaction notes

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