5-chloro-2-ethylbenzenamine synthesis
- Product Name:5-chloro-2-ethylbenzenamine
- CAS Number:3843-97-8
- Molecular formula:C8H10ClN
- Molecular Weight:155.62
116-69-8
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3843-97-8
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Yield:3843-97-8 100%
Reaction Conditions:
with iron(III) chloride;amino aminoalcohol in methanol at 20 - 80; for 5 h;Sealed tube;
Steps:
1.3
Step 3:ο a mixture of 4-chloro-l-ethyl-2-nitrobenzene (0.9 g, 4.9 mmol), iron (III) chloride (0.13 g, 0.49 mmol), and charcoal (80 mg, 6.6 mmol) in methanol (17 ml) was added hydrazine hydrate (0.95 ml, 20 mmol) in methanol (7 ml). The reaction mixture was stirred at rt as gas was evolved. When gas evolution ceased, the vial was sealed and heated at 80 deg C for 5 h (**pressure builds over time and vial needed to be vented frequently). The mixture was cooled to rt and filtered through celite washing with methanol, concentrated, and purified by silica gel chromatography (gradient 0 to 50% EtOAc/hexanes). The product, aniline 4, is a light yellow oil (quant.); 1H NMR (400 MHz, DMSO-d6) δ 6.86 (dd, = 8.0, 0.7 Hz, 1H), 6.59 (d, = 2.2 Hz, 1H), 6.44 (dd, 7 = 8.0, 2.2 Hz, 1H), 5.11 (s, 2H), 2.43 - 2.31 (m, 2H), 1.06 (t, J = 7.5 Hz, 3H).
References:
WO2016/106331,2016,A1 Location in patent:Paragraph 0222
589-16-2
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51529-96-5
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3663-34-1
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3843-97-8
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