Ethyl 4-amino-3-methyl­benzoate

Wen-Lan Song; Dan Wang; Xin-Hua Li; De-Cai Wang

doi:10.1107/S1600536808005989

. 2008 Apr 2;64(Pt 5):o785. doi: 10.1107/S1600536808005989

Ethyl 4-amino-3-methylbenzoate

Wen-Lan Song ^a, Dan Wang ^b, Xin-Hua Li ^a, De-Cai Wang ^a,^*

PMCID: PMC2961301 PMID: 21202278

Abstract

The asymmetric unit of the title compound, C₁₀H₁₃NO₂, contains two molecules which are linked via an N—H⋯N hydrogen bonds to form a dimer. These dimers are further linked via N—H⋯O intermolecular hydrogen bonds.

Related literature

For related literature, see: Baraldi et al. (1999 ▶, 2000 ▶, 2003 ▶, 2007 ▶); Wang et al. (2003 ▶); Zaffaroni et al. (2002 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C₁₀H₁₃NO₂
M _r = 179.21
Triclinic,
a = 8.0110 (16) Å
b = 8.7030 (17) Å
c = 15.835 (3) Å
α = 90.78 (3)°
β = 95.13 (3)°
γ = 114.34 (3)°
V = 1000.3 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 298 (2) K
0.30 × 0.20 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ▶) T _min = 0.975, T _max = 0.991
3874 measured reflections
3594 independent reflections
2146 reflections with I > 2σ(I)
R _int = 0.052
3 standard reflections every 200 reflections intensity decay: none

Refinement

R[F ² > 2σ(F ²)] = 0.074
wR(F ²) = 0.176
S = 1.02
3594 reflections
235 parameters
H-atom parameters constrained
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ▶); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo,1995 ▶); 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 datablocks I, global. DOI: 10.1107/S1600536808005989/er2050sup1.cif

e-64-0o785-sup1.cif^{(20.5KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808005989/er2050Isup2.hkl

e-64-0o785-Isup2.hkl^{(176.2KB, 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
N1—H1A⋯O2ⁱ	0.86	2.33	3.023 (5)	138
N1—H1B⋯N2	0.86	2.61	3.242 (5)	131
N2—H2C⋯O2ⁱ	0.86	2.35	3.160 (4)	157
N2—H2D⋯O4ⁱⁱ	0.86	2.15	2.967 (4)	158

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

Acknowledgments

The authors thank Dr Shan Liu for useful discussions.

supplementary crystallographic information

Comment

Ethyl 3-methyl-4-aminobenzoate is a material for preparing the important intermidates of bis-(2-haloethyl)aminophenyl substituted distamycin derivatives(Baraldi et al., 2007), which are used as antitumor alkylating and antiviral agents related to the known antibiotic distamycin A (Baraldi et al., 1999). Distamycin A belongs to the family of the pyrroleamidine antibiotics (Baraldi et al., 2000) and is reported to interact reversibly and selectively with DNA-AT sequences interfering with both replication and transcription (Baraldi et al., 2003). Bis-(2-haloethyl)aminophenyl substituted distamycin derivatives can therefore be used in a treatment to ameliorate a cancer (Wang et al., 2003). They may be administered to improve the condition of a patient having a leukaemia lymphoma, sarcoma, such as myeloblastic leukaemia, neuroblastoma, Wilm's tumor or malignant neoplasm of the bladder, breast, lung or thyroid. (Zaffaroni et al., 2002).

The molecular structure of (I) is shown in Fig. 1. The bond lengths and angles are within normal ranges (Allen et al., 1987).

The asymmetric unit of the title compound, contains two molecules which are linked via N—H···N hydrogen bonds to form dimers. In the crystals, molecules are linked via N—H···O Intermolecular hydrogen bonds (Table 1), which may be effective in the stabilization of the crystals.

Experimental

The title compound was prepared from 3-Methyl-4-aminobenzoic acid (15.2 g, 100 mmole) in ethanol (40.4 ml, 1000 mmole). After the solid has melted, concentrated hydrochloric acid (142 g, 120 ml) was added dropwise from a dropping funnel at 90°C, the the reaction mixture was cooled with ice and water and finaly the product was filtered by suction. Suitable crystals were obtained by evaporation of a methanol solution for about 3 d.