Anthranilic Acid → 4-Chloro-6-nitroquinazoline

HRID 1255968Notes

Reaction equation

HRID 1255968 reaction equation
NC1C=CC=CC=1C(O)=O.C(N)=O.[N+]([O-])(O)=O.S(=O)(=O)(O)O.O[C:24]1[C:33]2[C:28](=[CH:29][CH:30]=[C:31]([N+:34]([O-:36])=[O:35])[CH:32]=2)[N:27]=[CH:26][N:25]=1.S(Cl)([Cl:39])=O>>[Cl:39][C:24]1[C:33]2[C:28](=[CH:29][CH:30]=[C:31]([N+:34]([O-:36])=[O:35])[CH:32]=2)[N:27]=[CH:26][N:25]=1

Participants

7

Reactant 6

HCID 227Anthranilic AcidHCID 713FormamideHCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 24386Thionyl ChlorideHCID 178526470HCID 178526470, compound2×

Product 1

HCID 113562574-Chloro-6-nitroquinazoline

Procedure

In brief, 2-aminobezoic acid substituted by a reactive group (G in Scheme 3), is reacted with formamide, at 160° C., for 3 hours. The resulting 4-hydroxyquinazolinesubstituted by the reactive group is then reacted with a mixture of nitric acid and sulfuric acid, to thereby obtain 4-hydroxy-6-nitroquinazoline substituted by the reactive group. The reactive 4-hydroxy-6-nitroquinazoline is thereafter reacted with thionyl chloride, so as to obtain 4-chloro-6-nitroquinazoline substituted by a reactive group. In these compounds, the nitro group serves as a first reactive group and G is a second reactive group.

Sources & evidence

ORD record
ord-52fc9c2c1b9944b4aa7059f7955d5084
Source dataset
uspto-grants-2013_06
Patent number
US08461166B2

Reaction notes

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