Ethyl 3-amino-4-[(2-hy­droxy­ethyl)­amino]benzoate

Natarajan Arumugam; Aisyah Saad Abdul Rahim; Shafida Abd Hamid; Mohd Mustaqim Rosli; Hoong-Kun Fun

doi:10.1107/S1600536810029077

. 2010 Jul 31;66(Pt 8):o2141. doi: 10.1107/S1600536810029077

Ethyl 3-amino-4-[(2-hydroxyethyl)amino]benzoate

Natarajan Arumugam ^a, Aisyah Saad Abdul Rahim ^a,^‡, Shafida Abd Hamid ^b, Mohd Mustaqim Rosli ^c, Hoong-Kun Fun ^c,^*,^§

PMCID: PMC3007246 PMID: 21588428

Abstract

In the crystal structure of the title compound, C₁₁H₁₆N₂O₃, molecules are linked by one O—H⋯N and two N—H⋯O intermolecular hydrogen bonds into a three-dimensional network, which incorporates R ₂ ²(14) and R ₂ ²(16) graph-set motifs.

Related literature

For the biological activity of amino benzoic acid and benzimidazole derivatives, see: Kumar et al. (2003 ▶); Stefan et al. (2002 ▶); Pan et al. (1999 ▶). For related structures, see: Narendra Babu et al. (2009 ▶); Abdul Rahim et al. (2010 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C₁₁H₁₆N₂O₃
M _r = 224.26
Monoclinic,
a = 23.2300 (5) Å
b = 14.5914 (4) Å
c = 7.5815 (1) Å
β = 108.931 (1)°
V = 2430.81 (9) Å³
Z = 8
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 296 K
0.55 × 0.37 × 0.25 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.953, T _max = 0.978
26584 measured reflections
3739 independent reflections
2597 reflections with I > 2σ(I)
R _int = 0.035

Refinement

R[F ² > 2σ(F ²)] = 0.045
wR(F ²) = 0.134
S = 1.02
3739 reflections
162 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.16 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810029077/lh5088sup1.cif

e-66-o2141-sup1.cif^{(17.5KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810029077/lh5088Isup2.hkl

e-66-o2141-Isup2.hkl^{(183.4KB, hkl)}

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
O1—H1O1⋯N2ⁱ	0.846 (15)	2.017 (15)	2.8628 (14)	178.4 (14)
N2—H1N2⋯O3ⁱⁱ	0.880 (19)	2.145 (19)	3.0083 (16)	167.0 (13)
N2—H2N2⋯O1ⁱⁱⁱ	0.907 (15)	2.113 (15)	2.9800 (14)	159.7 (13)

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) .

Acknowledgments

NA, ASAR and SAH gratefully acknowledge the Ministry of Science, Technology and Innovations (MOSTI) Grant 304/PFARMASI/650512/I121 and the FRGS Grant (FRGS0510–119) for funding the synthetic chemistry work. NA thanks Universiti Sains Malaysia for the award of postdoctoral fellowship. HKF and MMR thank Universiti Sains Malaysia (USM) for the Research University Golden Goose Grant (1001/PFIZIK/811012).

supplementary crystallographic information

Comment

Amino benzoic acid derivatives are important intermediates for the synthesis of various heterocyclic compounds of pharmacological interests (Kumar et al., 2003). The synthesis of novel benzimidazole derivatives such as 2-aminomethyl benzimidazoles (Stefan et al., 2002) and oxobenzimidazoles (Pan et al., 1999) are commonly accessed via aminobenzoic acid derivatives. As part of an ongoing study on such compounds, we present the crystal structure of the title compound (I), which was an intermediate in a synthesis.

In the title molecule (Fig. 1), the bond lengths and angles are within normal ranges and are similiar to those in related structures (Narendra Babu et al., 2009; Abdul Rahim et al., 2010). The benzoate group is essentially planar with a maximum deviation of -0.006 (1) for atom C4.

In the crystal structure, molecules are linked by intermolecular N2—H1N2···O3ⁱⁱ, N2—H2N2···O1ⁱⁱⁱ and O1—H1O1···N2ⁱ hydrogen bonds (see Table 1 for symmetry codes) into a three-dimensional network with R₂²(14) and R₂²(16) graph-set motifs (Bernstein et al., 1995).

Experimental

Ethyl 4-(2-hydroxyethylamino)-3-nitro-benzoate (0.5 g, 1.96 mmol), ammonium formate (0.4 g, 6.8 mmol) and palladium on carbon (250 mg) were mixed in ethanol. The reaction mixture was irradiated under microwave conditions at 373K for 2 minutes. After completion, the reaction mixture was filtered through celite and the filtrate was concentrated under reduced pressure to yield the crude product. The product was recrystallised from EtOAc to afford the title compound as colourless crystals.