Anthranilic Acid → Anthranil

HRID 1647271Notes

Reaction equation

[C:1]([OH:10])(=O)[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[NH2:4].[C:11](OC(=O)C)(=[O:13])[CH3:12]>>[C:11]([C:1]1[O:10][N:4]=[C:3]2[C:2]=1[CH:8]=[CH:7][CH:6]=[CH:5]2)(=[O:13])[CH3:12].[N:4]1[O:10][CH:1]=[C:2]2[C:3]=1[CH:5]=[CH:6][CH:7]=[CH:8]2

Participants

Reactant 2

HCID 227Anthranilic Acid

HCID 7918Acetic Anhydride

Product 2

HCID 67498Anthranil

HCID 59777126HCID 59777126, compound

Procedure

reacting a compound of the formula ##STR85## wherein L is a leaving group, with a hydroxylamine hydrochloride to form an isonitrosoacetanilide compound of the formula ##STR86## (2) treating the isonitrosoacetanilide compound of step (1) with acid, followed by addition of ice and purification with alcohol, to obtain an isatin compound of the formula ##STR87## (3) reacting the isatin compound of step (2) with an aqueous basic peroxide to form an anthranilic acid compound of the formula ##STR88## (4) reacting the anthranilic acid compound of step (3) with acetic anhydride to form an acetylanthranil compound of the formula ##STR89## (5) treating the acetylanthranil compound of step (4) with alcohol, followed by acid, to obtain a compound of the formula ##STR90## and (6) reacting the product of step (5) with chloroformamidine hydrochloride to obtain a quinazoline compound of the formula ##STR91##

Sources & evidence

ORD record: ord-d1916b268bc64d95959f95e79a9963cd
Source dataset: uspto-grants-1995_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05430148

Reaction notes

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