N-Acetylanthranilic acid

N-Acetylanthranilic acid

Names
IUPAC name 2-Acetamidobenzoic acid
Other names 2-Acetamidobenzoic acid; 2-Carboxyacetanilide; o-Acetoaminobenozic acid; Acetylanthranilic acid; 2-(Acetylamino)benzoic acid
Identifiers
CAS Number	89-52-1
ChEBI	CHEBI:36555
ChemSpider	6705
Jmol interactive 3D	Image
PubChem	6971
InChI InChI=1S/C9H9NO3/c1-6(11)10-8-5-3-2-4-7(8)9(12)13/h2-5H,1H3,(H,10,11)(H,12,13) Key: QSACCXVHEVWNMX-UHFFFAOYSA-N InChI=1/C9H9NO3/c1-6(11)10-8-5-3-2-4-7(8)9(12)13/h2-5H,1H3,(H,10,11)(H,12,13) Key: QSACCXVHEVWNMX-UHFFFAOYAX
SMILES CC(=O)NC1=CC=CC=C1C(=O)O
Properties
Chemical formula	C9H9NO3
Molar mass	179.18 g·mol^−1
Density	1.36 g/mL
Melting point	184 to 186 °C (363 to 367 °F; 457 to 459 K)
Boiling point	399 °C (750 °F; 672 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

N-Acetylanthranilic acid is an organic compound with the molecular formula C₉H₉NO₃. It is an intermediate product in catabolism of quinaldine in Arthrobacter sp., and is further metabolized to anthranilic acid.^[1][2]

N-Acetylanthranilic acid can be synthesized from 2-bromoacetanilide via palladium-catalyzed carbonylation in tri-n-butylamine-water at 110-130 °C, under 3 atm of carbon monoxide.^[3]

N-Acetylanthranilic acid exhibits triboluminescence when crushed. The fractured crystals have large electrical potentials between areas of high and low charge. When the electrons suddenly migrate to neutralize these potentials, flashes of deep blue light are created.

In the United States, it is a Drug Enforcement Administration-controlled Table I illicit drug precursor,^[4] because it has been used in the synthesis of methaqualone.

See also

• Acedoben

References

1. Hund HK, de Beyer A, Lingens F. (1990). "Microbial metabolism of quinoline and related compounds. VI. Degradation of quinaldine by Arthrobacter sp". Biol Chem Hoppe Seyler 371 (10): 1005–1008. doi:10.1515/bchm3.1990.371.2.1005. PMID 2076195.
2. Overhage J, et al. (2005). "Identification of large linear plasmids in Arthrobacter spp. encoding the degradation of quinaldine to anthranilate". Microbiology 151 (2): 491–500. doi:10.1099/mic.0.27521-0. PMID 15699198.
3. Donald Valentine, Jefferson W. Tilley, Ronald A. LeMahieu (1981). "Practical, catalytic synthesis of anthranilic acids". Journal of Organic Chemistry 46 (22): 4614–4617. doi:10.1021/jo00335a075.
4. Title 21 Code of Federal Regulations