2-Benzyl-3-hy­droxy-3-methyl-2,3-dihydro-1H-isoindol-1-one

Hong-Yao Wang; Jing-Kui Yang

doi:10.1107/S1600536812021575

. 2012 May 19;68(Pt 6):o1795. doi: 10.1107/S1600536812021575

2-Benzyl-3-hydroxy-3-methyl-2,3-dihydro-1H-isoindol-1-one

Hong-Yao Wang ^a,^*, Jing-Kui Yang ^a

PMCID: PMC3379372 PMID: 22719570

Abstract

In the title compound, C₁₆H₁₅NO₂, the isoindoline ring system is approximately planar (mean deviation = 0.0186 Å) and makes a dihedral angle of 61.91 (4)° with the phenyl ring. In the crystal, molecules form inversion dimers via pairs of O—H⋯O hydrogen bonds.

Related literature

For background to the synthesis of the title compound, see: Griffiths et al. (1983 ▶); For its applications in synthesis, see: Winn & Zaugg (1968 ▶); Katsuhiko et al. (2006 ▶). For related structures, see: Wang et al. (2008 ▶); Orzeszko et al. (1998 ▶); Liu et al. (2009 ▶); Rosamilia et al. (2002 ▶).

Experimental

Crystal data

C₁₆H₁₅NO₂
M _r = 253.29
Monoclinic,
a = 11.093 (4) Å
b = 11.604 (4) Å
c = 21.226 (7) Å
β = 101.777 (5)°
V = 2674.7 (15) Å³
Z = 8
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 153 K
0.47 × 0.34 × 0.23 mm

Data collection

Rigaku AFC10/Saturn724+ diffractometer
11602 measured reflections
3479 independent reflections
2673 reflections with I > 2σ(I)
R _int = 0.032

Refinement

R[F ² > 2σ(F ²)] = 0.042
wR(F ²) = 0.114
S = 1.11
3479 reflections
177 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Data collection: CrystalClear (Rigaku, 2008 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812021575/nr2026sup1.cif

e-68-o1795-sup1.cif^{(22.2KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812021575/nr2026Isup2.hkl

e-68-o1795-Isup2.hkl^{(170.7KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812021575/nr2026Isup3.cml

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

Enhanced figure: interactive version of Fig. 1

Enhanced figure: interactive version of Fig. 2

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

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1O⋯O2ⁱ	0.960 (15)	1.836 (15)	2.7938 (14)	175.3 (12)

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Symmetry code: (i) Inline graphic .

Acknowledgments

We thank the National Natural Science Foundation of China and the Laboratory of Molecular Nanostructure and Nanotechnology, Institute of Chemistry, Chinese Academy of Sciences, for financial support.

supplementary crystallographic information

Comment

The title compound was obtained as a byproduct in the preparation of 2-benzyl-1,1,3,3-tetramethylisoindoline, an important intermediate in the synthesis of the radical 1,1,3,3-Tetramethylisoindolin-2-yloxyl (TMIO), which is used as spin probe and radical scavenger (Griffiths et al., 1983). The title compound can be applied in the synthesis of heterocyclic amines through intramolecular amidoalkylation (Winn & Zaugg, 1968) and anionic ring-enlarging reaction (Katsuhiko et al., 2006).

The molecular structure of the title compound is shown in Fig. 1 and there are some similiar stuctures reported before (Wang et al., 2008; Orzeszko et al., 1998; Liu et al., 2009; Rosamilia et al., 2002). In the molecule, the isoindol ring system is approximately planar [mean deviation = 0.0186 Å] and has a dihedral angle of 61.91 (4)° with the benzene ring. In the crystal (Fig. 2), molecules form centrosymmetric dimers via pairs of O—H···O hydrogen bonds (Table 1).

Experimental

1.4 ml me thyl magnesium bromide solution (3 M in ether) was added to a 25 ml round-bottom flask filled with nitrogen and heated to 60 °C. A solution of N-benzylphthalimides (500 mg, 2.11 mmol) in toluene (15 ml) was added dropwise with stirring at a sufficient rate to maintain this temperature. When the addition was complete, the solution was heated to 110 °C and maintained at this temperature for 4 h. The reaction mixture was cooled to room temperature and petroleum was added. The mixture turned purple after stirring in air for 12 h. At the end, the mixture was filtered on celite and the filtrate obtained was dried, giving a precipitate which was separated by column chromatography on silica gel (eluent: ethyl acetate/petroleum ether, 1:3). The title compound was obtained as a colorless solid (123 mg, 23%) and evaporation of a solution in ethanol for 24 h afforded colorless single crystals suitable for X-ray diffraction.