* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Reference:
[1] Journal of Organic Chemistry, 1961, vol. 26, p. 3214 - 3216
[2] Molecular Pharmacology, 2013, vol. 84, # 5, p. 726 - 735
2
[ 7499-73-2 ]
[ 90767-01-4 ]
Yield
Reaction Conditions
Operation in experiment
93%
With sulfuric acid In ethanol at 20℃; for 4 h;
A solution of 1-(acethylamino)-4-bromo-2-nitronaphthalene (535 mg, 1.73 mmol) in 50 percent H2SO4 (10 ml) and EtOH (10 ml) was stirredat ambient temperature for 4hrs. The suspension was washed with diethyl ether. The product(93 percent, orange solid) was filtered and dried in vacuo. 1H – NMR (400 MHz, CDCl3) δ 8.47 (s,1H), 8.23 (d, J = 8.4 Hz, 1H), 7.99 (d, J = 8.4 Hz, 1H), 7.78 (dd, J = 8.2, 7.2 Hz, 1H), 7.65(dd, J = 8.1, 7.3 Hz, 1H), 7.37 (bs, 2H)
Reference:
[1] Molecular Pharmacology, 2013, vol. 84, # 5, p. 726 - 735
[2] Justus Liebigs Annalen der Chemie, 1876, vol. 183, p. 250
[3] Journal of the Chemical Society, 1943, p. 321
[4] Justus Liebigs Annalen der Chemie, 1876, vol. 183, p. 250
[5] Journal of the Chemical Society, 1892, vol. 61, p. 769
[6] Chem. News J. Ind. Sci., 1892, vol. 65, p. 59[7] Chemische Berichte, 25 Ref. <1892>,750,
[8] Journal of the Chemical Society, 1885, vol. 47, p. 523[9] Journal of the Chemical Society, 1895, vol. 67, p. 912
[10] Journal of Organic Chemistry, 1961, vol. 26, p. 3214 - 3216
3
[ 64-17-5 ]
[ 7499-73-2 ]
[ 7664-41-7 ]
[ 90767-01-4 ]
Reference:
[1] Justus Liebigs Annalen der Chemie, 1876, vol. 183, p. 250
A solution of 1-(acethylamino)-4-bromo-2-nitronaphthalene (535 mg, 1.73 mmol) in 50 % H2SO4 (10 ml) and EtOH (10 ml) was stirredat ambient temperature for 4hrs. The suspension was washed with diethyl ether. The product(93 %, orange solid) was filtered and dried in vacuo. 1H - NMR (400 MHz, CDCl3) delta 8.47 (s,1H), 8.23 (d, J = 8.4 Hz, 1H), 7.99 (d, J = 8.4 Hz, 1H), 7.78 (dd, J = 8.2, 7.2 Hz, 1H), 7.65(dd, J = 8.1, 7.3 Hz, 1H), 7.37 (bs, 2H)
80%
With hydrogenchloride; In tetrahydrofuran; ethanol; water; for 8h;Reflux; Inert atmosphere;
In a two-necked flask, Compound 2-1 (38.0 g, 122.9 mmol), 2M HCl (246 ml), THF (500 ml) 250 ml of EtOH were heated under reflux conditions in an argon atmosphere for 8 hours.After completion of the reaction, the reaction mixture was cooled to room temperature and the organic solvent was concentrated under reduced pressure.The concentrate was neutralized with aqueous 2M NaOH, transferred to a separatory funnel and extracted with CH2Cl2. The extract was dried over MgSO4 and then purified by silica gel column chromatography to obtain 28.4 g (yield 80%, MS [M + H] + = 267) of Compound 4-2 as a solid.
80%
With hydrogenchloride; In tetrahydrofuran; ethanol; water; for 8h;Inert atmosphere; Reflux;
Compound 4-1 (38.0 g, 122.9 mmol), 2M HCl (246 ml, 491.7 mmol), THF (500 ml) and EtOH (250 ml) were heated under reflux in an argon atmosphere for 8 hours. After completion of the reaction, the reaction mixture was cooled to room temperature and the organic solvent was concentrated under reduced pressure. The concentrate was neutralized with aqueous 2M NaOH, transferred to a separatory funnel and extracted with CH2Cl2. The extract was dried over MgSO4 and then purified by silica gel column chromatography to obtain 28.4 g (yield 80%, MS[M+H]+=267) of Compound 4-2 as a solid.
80%
With hydrogenchloride; In tetrahydrofuran; ethanol; water; for 8h;Inert atmosphere; Reflux;
To the two-necked flask Compound 4-1 (38.0g, 122.9mmol), 2M HCl (246ml, 491.7mmol), THF (500ml), and EtOH (250ml) were heated in an argon atmosphere under reflux for 8 hours. After the reaction was completed, the organic solvent was concentrated under reduced pressure after cooling to room temperature. The concentrate was neutralized with 2M NaOH aqueous solution and then transferred to a separatory funnel and extracted with CH2Cl2. The extract was dried over MgSO 4 and purified by silica gel column chromatography to obtain 28.4 g of solid compound 4-2 (yield 80%
With bismuth (III) nitrate pentahydrate; In dichloromethane; at 20℃; for 5h;
To the three-necked flask were added 4-bromonaphthalen-1-amine (35.0 g, 157.6 mmol), Bi (NO3) 3 .5H2O (76.4 g, 157.6 mmol), CH2Cl2 800 ml, acetic anhydride (89 ml, 945.6 mmol) And the mixture was stirred at room temperature for 5 hours.When the reaction was completed, a saturated aqueous solution of NaHCO3 was added, and the mixture was transferred to a separatory funnel and extracted with ethyl acetate. The extract was dried over MgSO4,The residue was purified by silica gel column chromatography to obtain 38.0 g (yield 78%) of Compound 4-1 as a solid.
78%
With bismuth (III) nitrate pentahydrate; In dichloromethane; at 20℃; for 5h;
4-bromonaphthalen-1-amine (35.0 g, 157.6 mmol) and Bi(NO3)3.5H2O (76.4 g, 157.6 mmol) CH2Cl2 (800 ml), acetic anhydride (89 ml, 945.6 mmol)And the mixture was stirred at room temperature for 5 hours.After the reaction was completed, a saturated aqueous solution of NaHCO3 was added, and the mixture was transferred to a separatory funnel and extracted with ethyl acetate. The extract was dried over MgSO4 and then purified by silica gel column chromatography to obtain 38.0 g (yield 78%, MS[M+H]+=309) of Compound 4-1 as a solid.
78%
With bismuth (III) nitrate pentahydrate; In dichloromethane; at 20℃; for 5h;
In a three-necked flask add 4-bromonaphthalen-1-amine (35.0g, 157.6mmol) and Bi (NO3) 3 · 5H2O (76.4g, 157.6mmol), CH2Cl2 (800ml), acetic anhydride (89ml, 945.6mmol)It was stirred at room temperature for 5 hr. After the reaction was completed, saturated NaHCO3 aqueous solution was added, transferred to a separatory funnel, and extracted with ethyl acetate. The extract was dried over MgSO 4 and purified by silica gel column chromatography to obtain 38.0 g of solid compound 4-1 (yield 78%