تفاعل #1449734

معادلة التفاعل

(2E,4E)-5-(2-nitrophenyl)penta-2,4-dienoic acid

tetrahydrofuran

triethylamine

methyl 6-aminohexanoate hydrochloride

→

title compound

المردود 89.5%

(2E,4E)-6-[5-(2-Nitrophenyl)penta-2,4-dienoylamino]hexanoic acid methyl ester

المردود 89.5%

ظروف التفاعل

المعالجة

1. 1
   أخرىThe solvent was evaporated, to the obtained residue water (15 ml)
2. 2
   workup.ADDITIONwas added
3. 3
   ترشيحthe precipitate was filtered off
4. 4
   غسيلThe precipitate was washed with an additional amount of water
5. 5
   أخرىdried

الإجراء التجريبي

To a solution of (2E,4E)-5-(2-nitrophenyl)penta-2,4-dienoic acid (9a) (0.44 g, 2.0 mmol) in dry tetrahydrofuran (10 ml) 1,1′-carbonyldiimidazole (0.36 g, 2.2 mmol) (Sigma-Aldrich) was added and the mixture was stirred for 1 hour at ambient temperature. To the reaction mixture triethylamine (0.30 g 3.0 mmol) and methyl 6-aminohexanoate hydrochloride (10) (0.40 g, 2.2 mmol) successively were added and the resultant suspension was stirred for 6 hour at ambient temperature. The solvent was evaporated, to the obtained residue water (15 ml) was added and the precipitate was filtered off. The precipitate was washed with an additional amount of water and dried to give the title compound (0.62 g, 89%) as a yellow solid, m.p. 115-117° C. 1H NMR (DMSO-d6, HMDSO), δ: 1.10-1.79 (6H, m, CH2); 2.29 (2H, J=7.0 Hz, CH2); 3.17 (2H, q, J=5.6 Hz, CH2N); 3.60 (3H, s); 6.24 (1H, d, J=14.8 Hz, CH); 7.04-8.10 (8H, m, CH—CH═CH, C6H4, NH).

المصدر