1-(4-METHOXY-PHENYL)-1H-PYRAZOL-3-YLAMINE synthesis
- Product Name:1-(4-METHOXY-PHENYL)-1H-PYRAZOL-3-YLAMINE
- CAS Number:76091-01-5
- Molecular formula:C10H11N3O
- Molecular Weight:189.21
60838-50-8
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19501-58-7
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$7.00/250mg
76091-01-5
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$45.00/10mg
Yield:76091-01-5 85%
Reaction Conditions:
with sodium ethanolate in ethanol at 150; for 2 h;Sealed tube;Microwave irradiation;
Steps:
7 3-Amino-1-phenyl-1H-pyrazole (11a)
3.7
3-Amino-1-(4-methoxyphenyl)-1H-pyrazole (11b)
A solution of 4-(methoxyphenyl)hydrazine hydrochloride (2e·HCl) (0.17 g, 1.2 mmol), 3-methoxyacrylonitrile (1a) (0.20 mL, 2.4 mmol) and NaOEt (0.41 g, 4.8 mmol) in dry EtOH (3 mL) was irradiated at 150 °C for 2 h in a sealed, pressure-rated Pyrex tube (10 mL) using a CEM Discover microwave synthesizer by moderating the initial power (150 W).
The mixture was cooled by passing a stream of compressed air through the microwave cavity and H2O was added (10 mL).
The aqueous layer was extracted with EtOAc (2*20 mL) and the organic extracts were combined, washed with brine, dried (MgSO4) and evaporated in vacuo.
Purification by column chromatography on silica, eluting with hexane-EtOAc (1:3 v/v), gave the title compound (0.19 g, 85%) as a yellow solid, mp 146-149 °C (found: 189.0900. C10H11N3O [M] requires 189.0902); FTIR (KBr)/cm-1 νmax 3360 (NH), 1556, 1310, 1299, 1069; 1H NMR (400 MHz; DMSO-d6) δ 8.00 (1H, d, J 2.5, H-5), 7.55 (2H, d, J 9, H-2'/H-6'), 6.95 (2H, d, J 9, H-3'/H-5'), 5.67 (1H, d, J 2.5, H-4), 4.97 (2H, br s, exch. D2O, NH2), 3.76 (3H, s, Me); 13C NMR (126 MHz; DMSO-d6) δ 157.1 (C), 156.5 (C), 134.5 (C), 127.9 (CH), 118.3 (CH), 114.8 (CH), 95.8 (CH), 55.8 (Me); LRMS (EI) m/z (rel intensity) 189 (M
References:
Bagley, Mark C.;Baashen, Mohammed;Paddock, Victoria L.;Kipling, David;Davis, Terence [Tetrahedron,2013,vol. 69,# 39,p. 8429 - 8438]
1820-80-0
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696-62-8
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$5.00/1g
76091-01-5
16 suppliers
$45.00/10mg
16907-09-8
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$411.00/1g