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58279

Isatoic anhydride

Name: Isatoic anhydride
Brand: SIAL

technical, ≥94% (HPLC)

Synonym(s):

3,1-Benzoxazine-2,4(1H)-dione, Anthranilic acid N-carboxylic acid anhydride

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About This Item

Empirical Formula (Hill Notation):

C₈H₅NO₃

CAS Number:

118-48-9

Molecular Weight:

163.13

Beilstein:

136786

EC Number:

204-255-0

MDL number:

MFCD00006700

UNSPSC Code:

12162002

PubChem Substance ID:

329758412

vapor density

5.6 (vs air)

grade

technical

Assay

≥94% (HPLC)

mp

233 °C (dec.) (lit.)

SMILES string

O=C1Nc2ccccc2C(=O)O1

InChI

1S/C8H5NO3/c10-7-5-3-1-2-4-6(5)9-8(11)12-7/h1-4H,(H,9,11)

InChI key

TXJUTRJFNRYTHH-UHFFFAOYSA-N

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Other Notes

Review; Reagent for 2-aminobenzoylations

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G.M. Coppola

Synthesis, 505-505 (1980)

M.C. Venuti

Synthesis, 266-266 (1982)

Palladium-catalyzed regioselective carbonylation of C-H bonds of N-alkyl anilines for synthesis of isatoic anhydrides.

Zheng-Hui Guan et al.

Journal of the American Chemical Society, 134(42), 17490-17493 (2012-10-12)

A Pd-catalyzed regioselective C-H bond carbonylation of N-alkyl anilines for the synthesis of isatoic anhydrides has been developed. The key Pd-catalyst intermediate has been isolated and characterized. This novel Pd-catalyzed carbonylation reaction tolerates a wide range of functional groups and

A new cascade reaction: concurrent construction of six and five membered rings leading to novel fused quinazolinones.

K Siva Kumar et al.

Organic & biomolecular chemistry, 10(15), 3098-3103 (2012-03-10)

A one-pot cascade reaction has been developed leading to the concurrent construction of six and five membered fused N-heterocyclic rings of indazolo[3,2-b]quinazolinones. The methodology involved the reaction of isatoic anhydride, a hydrazine and o-iodo benzaldehyde in the presence of Pd(PPh(3))(4)

1,3-Dipolar cycloaddition-decarboxylation reactions of an azomethine ylide with isatoic anhydrides: formation of novel benzodiazepinones.

Asha M D'Souza et al.

Organic letters, 13(3), 486-489 (2010-12-24)

A nonstabilized azomethine ylide reacts with a wide range of substituted isatoic anhydrides to afford novel 1,3-benzodiazepin-5-one derivatives, which are generally isolated in high yield. The transformations involve 1,3-dipolar cycloaddition reactions of the ylide with the anhydrides to give transient

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