4-Hy­droxy-1-methyl-3-phenyl­quinolin-2(1H)-one

Stanislav Kafka; Andrej Pevec; Karel Proisl; Roman Kimmel; Janez Košmrlj

doi:10.1107/S1600536813000226

. 2013 Jan 12;69(Pt 2):o231. doi: 10.1107/S1600536813000226

4-Hydroxy-1-methyl-3-phenylquinolin-2(1H)-one

Stanislav Kafka ^a, Andrej Pevec ^b,^*, Karel Proisl ^a, Roman Kimmel ^a, Janez Košmrlj ^b

PMCID: PMC3569765 PMID: 23424511

Abstract

In the title compound, C₁₆H₁₃NO₂, the quinoline system is approximately planar with a maximum deviation from the least-squares plane of 0.059 (1) Å for the N atom. The phenyl ring is rotated by 62.16 (4)° with respect to the plane of the quinoline system. In the crystal, O—H⋯O hydrogen bonds link molecules into infinite chains running along the b-axis direction.

Related literature

For the preparation of the title compound and other 4-hydroxyquinolin-2-ones, see: Baumgarten & Kärgel (1927 ▶); Lange et al., (2001 ▶); Martensson & Nilsson (1960 ▶); Bezuglyi et al. (1992 ▶). For synthetic utilization of the title compound, see: Kafka et al. (2002 ▶); Klásek et al. (2002 ▶).

Experimental

Crystal data

C₁₆H₁₃NO₂
M _r = 251.27
Monoclinic,
a = 6.1787 (2) Å
b = 8.2696 (2) Å
c = 12.3665 (4) Å
β = 101.632 (2)°
V = 618.89 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 293 K
0.50 × 0.25 × 0.10 mm

Data collection

Nonius KappaCCD area-detector diffractometer
Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997 ▶) T _min = 0.957, T _max = 0.991
2580 measured reflections
1479 independent reflections
1235 reflections with I > 2σ(I)
R _int = 0.017

Refinement

R[F ² > 2σ(F ²)] = 0.039
wR(F ²) = 0.102
S = 1.02
1479 reflections
174 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.13 e Å⁻³
Δρ_min = −0.16 e Å⁻³

Data collection: COLLECT (Nonius, 1998 ▶); cell refinement: DENZO and SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO and SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶) and DIAMOND (Brandenburg, 1999 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶).

Supplementary Material

Click here for additional data file.^{(23.2KB, cif)}

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813000226/fy2079sup1.cif

e-69-0o231-sup1.cif^{(23.2KB, cif)}

Click here for additional data file.^{(71.4KB, hkl)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813000226/fy2079Isup2.hkl

e-69-0o231-Isup2.hkl^{(71.4KB, hkl)}

Click here for additional data file.^{(5KB, cml)}

Supplementary material file. DOI: 10.1107/S1600536813000226/fy2079Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2O⋯O1ⁱ	0.82	1.89	2.655 (2)	156

Open in a new tab

Symmetry code: (i) Inline graphic .

Acknowledgments

This study was supported by the internal grant of the TBU in Zlin (No. IGA/FT/2012/043) funded from the resources of specific university research and the Slovenian Research Agency (Project P1–0230–0103 and Joint Project BI—CZ/07–08–018). This work was also partly supported through the infrastructure of the EN–FIST Centre of Excellence, Ljubljana.

supplementary crystallographic information

Comment

The title compound, (I) (Fig. 1), was first prepared by the thermal condensation of diethyl phenylmalonate with N-methylaniline (Baumgarten & Kärgel 1927). This reaction, performed with various malonates and anilines, is still the most widely used general method for the preparation of 4-hydroxyquinolin-2-ones, including compound I. The performance of the reaction under microwave irradiation was described by Lange et al. (2001). Among other approaches to the preparation of compound I and other 4-hydroxyquinoline-2-diones, intramolecular condensations of 2-acylaminobenzoates could be particularly feasible (Martensson & Nilsson, 1960; Bezuglyi et al., 1992). Recently, compound I was utilized for the preparation of the corresponding 3-bromo- and 3-chloro-1-methyl-3-phenylquinoline-2,4(1H,3H)-diones, from which other compounds were prepared by nucleophilic substitution of the halogen atom (Kafka et al., 2002; Klásek et al., 2002).

In the crystal structure of the title compound (I) (Fig. 2) 4-hydroxy-1-methyl-3-phenylquinolin-2(1H)-one molecules are connected by intermolecular O—H···O hydrogen bonds between the hydroxyl and carbonyl groups (Table 1). These connections form linear chains along the b-axis in the crystal structure.

Experimental

Title compound was prepared according to a modified procedure published by Baumgarten & Kärgel (1927). A mixture of N-methylaniline (10.7 g, 100 mmol) and diethyl phenylmalonate (24.8 g, 105 mmol) was gradually heated in a Wood's metal bath at 200–290 °C for 4.5 h (until the distillation of ethanol stopped; reached 8.57 g, i.e. 93% of theoretical mass of distillate). The hot reaction mixture was poured into a mortar, crushed after cooling and dissolved in the mixture of aqueous sodium hydroxide solution (0.5 M, 300 ml) and toluene (50 ml). The aqueous phase was separated, washed with toluene, shortly stirred with active carbon, filtered and acidified by addition of 10% hydrochloric acid to Kongo red. The precipitated white solid was filtered off, washed with water and air dried affording 23.4 g (93% of theory) of crude product, m. p. 223–225 C. Crystallization of the crude product from ethanol afforded 20.1 g (80% of theoretical yield) of the title compound (I), m. p. 222–226 °C. In the literature (Martensson & Nilsson, 1960), the same m. p. is given.