2-amino-4-ethyl-5-methylbenzene-1,3-dicarbonitrile synthesis
- Product Name:2-amino-4-ethyl-5-methylbenzene-1,3-dicarbonitrile
- CAS Number:55525-92-3
- Molecular formula:C11H11N3
- Molecular Weight:185.23
123-11-5
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123-38-6
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109-77-3
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![[1,1'-Biphenyl]-2,4-dicarbonitrile, 3-amino-4'-methoxy-6-methyl-](/CAS/20210305/GIF/1338442-76-4.gif)
1338442-76-4
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55525-92-3
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Yield:1338442-76-4 77% ，55525-92-3 8%
Reaction Conditions:
with morpholine in N,N-dimethyl-formamide at 80; for 12 h;
Steps:
Preparation of 3-amino-4'-methoxy-6-methyl-[1,1'-biphenyl]-2,4-dicarbonitrile (2a)
To a mixture of propionaldehyde (2.00 g, 34.48 mmol), 4-methoxybenzaldehyde (3.75 g, 27.58 mmol) and malononitrile (4.55 g, 68.96 mmol) in dry DMF (20 mL) taken in a round bottom flask equipped with reflux condenser and guard tube, was added morpholine (6.60 g, 75.85 mmol) at 0 0C. The mixture was allowed to come to RT and then stirred at 80 0C for 12 h. It was then cooled to room temperature, diluted with ice-cold water (100 mL), extracted with ethyl acetate (3 x 75 mL), dried over Na2SO4, concentrated and purified by column chromatography on silica gel using pet ether-ethyl acetate (3% to 20% ethyl acetate in pet ether) as eluent to give 3-ethyl-4-methyl-2,6-dicyanoaniline (4)8d as a white solid in initial fractions (0.255 g, 8%). Further elution afforded pure 3-amino-4'-methoxy-6-methyl-[1,1'-biphenyl]-2,4-dicarbonitrile 2a as white solid (5.58 g, 77%), MP: 199 oC. IR (Chloroform): 1270, 1477, 1514, 1606, 1644, 2218, 2915, 3247, 3349, 3434 cm-1. 1H NMR (200 MHz, CDCl3): δ 2.05 (s, 3H), 3.87 (s, 3H), 5.07 (bs, 2H), 7.01 (d, J= 8Hz, 2H), 7.21 (d, J= 10Hz, 2H), 7.47 (s, 1H). 13C NMR (50 MHz, DMSO-d6): δ 18.8, 55.3, 96.1, 98.0, 114.1 (2C), 116.1, 116.7, 124.7, 129.4, 130.1 (2C), 138.9, 150.5, 151.1, 159.6. MS (ESI): m/z 262.14 (M-1).
References:
Sawargave, Sangmeshwer P.;Kudale, Ananada S.;Deore, Jaydeep V.;Bhosale, Dattatry S.;Divse, Jaisingh M.;Chavan, Subhash P.;Borate, Hanumant B. [Tetrahedron Letters,2011,vol. 52,# 42,p. 5491 - 5493] Location in patent:supporting information; experimental part
123-11-5
855 suppliers
$10.00/10g
123-38-6
428 suppliers
$14.00/5mL
109-77-3
430 suppliers
$10.00/5g
1338442-76-4
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55525-92-3
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4180-23-8
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