4-Ethoxy­pyridin-2-amine

Lihua Mao; Yan Chen

doi:10.1107/S1600536808024847

. 2008 Aug 13;64(Pt 9):o1749. doi: 10.1107/S1600536808024847

4-Ethoxypyridin-2-amine

Lihua Mao ^a,^*, Yan Chen ^b

PMCID: PMC2960701 PMID: 21201731

Abstract

The title compound, C₇H₁₀N₂O, crystallizes with two independent molecules in the asymmetric unit. The bond lengths and angles in the molecules are within normal ranges. The crystal structure is stabilized by intermolecular N—H⋯N hydrogen bonds, linking the two independent molecules into hydrogen-bonded dimers.

Related literature

For related literatures, see: Cai et al. (2006 ▶); Yale (1976 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C₇H₁₀N₂O
M _r = 138.17
Triclinic,
a = 9.167 (2) Å
b = 9.470 (2) Å
c = 9.541 (3) Å
α = 87.716 (3)°
β = 87.714 (4)°
γ = 64.189 (3)°
V = 744.8 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 298 (2) K
0.60 × 0.38 × 0.31 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T _min = 0.901, T _max = 0.974
3749 measured reflections
2582 independent reflections
2110 reflections with I > 2σ(I)
R _int = 0.018

Refinement

R[F ² > 2σ(F ²)] = 0.043
wR(F ²) = 0.123
S = 1.02
2582 reflections
182 parameters
H-atom parameters constrained
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.16 e Å⁻³

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); 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 local programs.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808024847/bx2167sup1.cif

e-64-o1749-sup1.cif^{(17.8KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808024847/bx2167Isup2.hkl

e-64-o1749-Isup2.hkl^{(126.8KB, 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
N2—H2B⋯N1ⁱ	0.86	2.19	3.029 (2)	164
N4—H4B⋯N3ⁱⁱ	0.86	2.16	3.013 (2)	173

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

supplementary crystallographic information

Comment

2-Amino-4-ethoxypyridine is a useful intermediate for the synthesis of various heterocyclic compounds (Cai et al., 2006; Yale, 1976). In this paper, we report the crystal structure of the title compound (I). The title compound crystallizes with two independent molecules in the asymmetric unit. All bond lengths are normal (Allen et al., 1987). Intermolecular N—H···N hydrogen bonds link the two independent molecules into hydrogen-bonded dimers. The crystal packing is further stabilized by van der Waals forces.

Experimental

2-amino-4-chloropyridine (12.9 g, 0.1 mol) and sodium ethoxide (12.8 g, 0.2 mol) were reacted in 100 ml ethanol in a stainless steel bomb at 150°C for 3 h. The desired compound was obtained as a slightly yellow solid in 50% yield (1.9 g). Crystals suitable for X-ray diffraction analysis were obtained by slow evaporation of a solution in a hexane/dichloromethane mixture (1:4 v/v) at room temperature over a period of one week.