Pyridine → 2H-1,2-Benzoxazin-3(4H)-one

HRID 2057111Notes

Reaction equation

HRID 2057111 reaction equation
CS(Cl)(=O)=[O:3].C(N(CC)CC)C.[NH:13]1[CH:17]=[CH:16][C:15]([C:18]([OH:20])=O)=N1.N1C=[CH:25][CH:24]=[CH:23][CH:22]=1>>[O:20]1[C:18]2[CH:22]=[CH:23][CH:24]=[CH:25][C:15]=2[CH2:16][C:17](=[O:3])[NH:13]1

Participants

5

Reactant 4

HCID 1049PyridineHCID 8471TriethylamineHCID 31297Methanesulfonyl chloride2×HCID 178524567HCID 178524567, compound

Product 1

HCID 199374482H-1,2-Benzoxazin-3(4H)-one

Procedure

Coupling of a pyrazolecarboxylic acid of Formula 6 wherein R4 is H with an anthranilic acid of Formula 7 provides the benzoxazinone of Formula 8. In Scheme 7, a benzoxazinone of Formula 8 is prepared directly via sequential addition of methanesulfonyl chloride in the presence of a tertiary amine such as triethylamine or pyridine to a pyrazolecarboxylic acid of Formula 6 wherein R4 is H, followed by the addition of an anthranilic, acid of Formula 7, followed by a second addition of tertiary amine and methanesulfonyl chloride.

Sources & evidence

ORD record
ord-b9671be7b8d04f35b03eda1225d3d7db
Source dataset
uspto-grants-2008_02
Patent number
US07335780B2

Reaction notes

Loading…