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

HRID 2117806Notes

Reaction equation

HRID 2117806 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.[C:21](O)(=O)[C:22]1C(=CC=[CH:27][CH:28]=1)N>N1C=CC=CC=1>[O:20]1[C:18]2[CH:21]=[CH:22][CH:28]=[CH:27][C:15]=2[CH2:16][C:17](=[O:3])[NH:13]1

Participants

6

Reactant 4

HCID 227Anthranilic AcidHCID 8471TriethylamineHCID 31297Methanesulfonyl chloride2×HCID 178524567HCID 178524567, compound

Product 1

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

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Coupling of a pyrazolecarboxylic acid of Formula 7 wherein R1 is H with an anthranilic acid of Formula 8 provides the benzoxazinone of Formula 9. In Scheme 9, a benzoxazinone of Formula 9 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 7 wherein R1 is H, followed by the addition of an anthranilic acid of Formula 8, followed by a second addition of tertiary amine and methanesulfonyl chloride.

Sources & evidence

ORD record
ord-8dacae34b6484334a0837b9839986c41
Source dataset
uspto-grants-2008_10
Patent number
US07442799B2

Reaction notes

Loading…