Naphtholactam

Naphtholactam is an organic compound derived from naphthalene. It is a tricyclic species consisting of a naphthalene core fused with a lactam (NH-CO-) at the 1,8-positions. The N-alkyl derivatives are commercially important.

Naphtholactam
Names
Preferred IUPAC name
Benzo[cd]indol-2(1H)-one
Other names
1,8-naphtholactam
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.004.523
EC Number
  • 204-973-4
  • InChI=1S/C11H7NO/c13-11-8-5-1-3-7-4-2-6-9(12-11)10(7)8/h1-6H,(H,12,13)
    Key: GPYLCFQEKPUWLD-UHFFFAOYSA-N
  • C1=CC2=C3C(=C1)C(=O)NC3=CC=C2
Properties
C11H7NO
Molar mass 169.183 g·mol−1
Appearance white solid
Melting point 181 °C (358 °F; 454 K)
Hazards
GHS labelling:
GHS07: Exclamation mark
Warning
H302
P264, P270, P301+P312, P330, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Dye precursor

It is a precursor to the dye anthanthrone via ring-opening to the amino carboxylic acid, which can be converted to the diazonium salt. Naphthostyril derivatives are also of interest in medicinal chemistry.[1] Naphthostyrils can be produced by metal-catalyzed cyclization of 1-naphthylamides.[2]

Chemical structure of typical naphtholactam dye.

N-Ethylnaphtholactam and related derivatives are precursors to many dyes. The lactam condenses with anilines in the presence of phosphorus oxychloride.[3]

References
  1. López-Rodríguez, María L.; Porras, Esther; Morcillo, M. José; Benhamú, Bellinda; Soto, Luis J.; Lavandera, José L.; Ramos, José A.; Olivella, Mireia; Campillo, Mercedes; Pardo, Leonardo (2003). "Optimization of the Pharmacophore Model for 5-HT7R Antagonism. Design and Synthesis of New Naphtholactam and Naphthosultam Derivatives". Journal of Medicinal Chemistry. 46 (26): 5638–5650. doi:10.1021/jm030841r. hdl:10637/5547. PMID 14667218.
  2. Ying, Jun; Fu, Lu-Yang; Zhong, Guoqiang; Wu, Xiao-Feng (2019). "Cobalt-Catalyzed Direct Carbonylative Synthesis of Free (NH)-Benzo[cd]indol-2(1H)-ones from Naphthylamides". Organic Letters. 21 (14): 5694–5698. doi:10.1021/acs.orglett.9b02037. PMID 31246481.
  3. Berneth, Horst (2008). "Methine Dyes and Pigments". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a16_487.pub2.
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