* 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] Canadian Journal of Chemistry, 1987, vol. 65, p. 2428 - 2433
3
[ 75-76-3 ]
[ 768-95-6 ]
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[ 768-91-2 ]
Reference:
[1] Journal of Organic Chemistry USSR (English Translation), 1983, p. 297 - 300[2] Zhurnal Organicheskoi Khimii, 1983, vol. 19, # 2, p. 339 - 343
[3] Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation), 1981, vol. 30, # 12, p. 2370[4] Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1981, # 12, p. 2839
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[ 768-90-1 ]
[ 75-76-3 ]
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Reference:
[1] Journal of Organic Chemistry USSR (English Translation), 1981, vol. 17, # 7, p. 1203 - 1208[2] Zhurnal Organicheskoi Khimii, 1981, vol. 17, # 7, p. 1357 - 1363
[3] Journal of Organic Chemistry USSR (English Translation), 1981, vol. 17, # 7, p. 1203 - 1208[4] Zhurnal Organicheskoi Khimii, 1981, vol. 17, # 7, p. 1357 - 1363
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[ 75-76-3 ]
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Reference:
[1] Journal of Organic Chemistry USSR (English Translation), 1981, vol. 17, # 7, p. 1203 - 1208[2] Zhurnal Organicheskoi Khimii, 1981, vol. 17, # 7, p. 1357 - 1363
[3] Journal of Organic Chemistry USSR (English Translation), 1981, vol. 17, # 7, p. 1203 - 1208[4] Zhurnal Organicheskoi Khimii, 1981, vol. 17, # 7, p. 1357 - 1363
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[ 75-76-3 ]
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Reference:
[1] Journal of Organic Chemistry USSR (English Translation), 1983, p. 297 - 300[2] Zhurnal Organicheskoi Khimii, 1983, vol. 19, # 2, p. 339 - 343
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[ 768-90-1 ]
[ 75-76-3 ]
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Reference:
[1] Journal of Organic Chemistry USSR (English Translation), 1983, p. 297 - 300[2] Zhurnal Organicheskoi Khimii, 1983, vol. 19, # 2, p. 339 - 343
[3] Journal of Organic Chemistry USSR (English Translation), 1983, p. 297 - 300[4] Zhurnal Organicheskoi Khimii, 1983, vol. 19, # 2, p. 339 - 343
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[ 75-76-3 ]
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Reference:
[1] Journal of Organic Chemistry USSR (English Translation), 1983, p. 297 - 300[2] Zhurnal Organicheskoi Khimii, 1983, vol. 19, # 2, p. 339 - 343
[3] Journal of Organic Chemistry USSR (English Translation), 1983, p. 297 - 300[4] Zhurnal Organicheskoi Khimii, 1983, vol. 19, # 2, p. 339 - 343
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Reference:
[1] Journal of Organic Chemistry USSR (English Translation), 1983, p. 297 - 300[2] Zhurnal Organicheskoi Khimii, 1983, vol. 19, # 2, p. 339 - 343
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[ 768-90-1 ]
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Reference:
[1] Journal of Organic Chemistry USSR (English Translation), 1983, p. 297 - 300[2] Zhurnal Organicheskoi Khimii, 1983, vol. 19, # 2, p. 339 - 343
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Reference:
[1] Canadian Journal of Chemistry, 1987, vol. 65, p. 2428 - 2433
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Reference:
[1] Canadian Journal of Chemistry, 1987, vol. 65, p. 2428 - 2433
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Reference:
[1] Angewandte Chemie - International Edition, 2013, vol. 52, # 44, p. 11564 - 11568[2] Angew. Chem., 2013, vol. 125, # 44, p. 11778 - 11782,5
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Reference:
[1] Journal of Organic Chemistry USSR (English Translation), 1983, p. 297 - 300[2] Zhurnal Organicheskoi Khimii, 1983, vol. 19, # 2, p. 339 - 343
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Reference:
[1] J. Appl. Chem. USSR (Engl. Transl.), 1984, vol. 57, # 7, p. 1545 - 1546[2] Zhurnal Prikladnoi Khimii (Sankt-Peterburg, Russian Federation), 1984, vol. 57, # 7, p. 1657 - 1659
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Reference:
[1] J. Appl. Chem. USSR (Engl. Transl.), 1984, vol. 57, # 7, p. 1545 - 1546[2] Zhurnal Prikladnoi Khimii (Sankt-Peterburg, Russian Federation), 1984, vol. 57, # 7, p. 1657 - 1659
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Reference:
[1] J. Appl. Chem. USSR (Engl. Transl.), 1984, vol. 57, # 7, p. 1545 - 1546[2] Zhurnal Prikladnoi Khimii (Sankt-Peterburg, Russian Federation), 1984, vol. 57, # 7, p. 1657 - 1659
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[ 702-79-4 ]
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Reference:
[1] J. Appl. Chem. USSR (Engl. Transl.), 1984, vol. 57, # 7, p. 1545 - 1546[2] Zhurnal Prikladnoi Khimii (Sankt-Peterburg, Russian Federation), 1984, vol. 57, # 7, p. 1657 - 1659
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[ 75-76-3 ]
[ 702-79-4 ]
[ 281-23-2 ]
[ 1687-36-1 ]
[ 707-35-7 ]
[ 768-91-2 ]
Reference:
[1] Journal of Organic Chemistry USSR (English Translation), 1983, p. 297 - 300[2] Zhurnal Organicheskoi Khimii, 1983, vol. 19, # 2, p. 339 - 343
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[ 75-76-3 ]
[ 935-56-8 ]
[ 702-79-4 ]
[ 281-23-2 ]
[ 1687-36-1 ]
[ 707-35-7 ]
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Reference:
[1] Journal of Organic Chemistry USSR (English Translation), 1983, p. 297 - 300[2] Zhurnal Organicheskoi Khimii, 1983, vol. 19, # 2, p. 339 - 343
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Reference:
[1] Journal of Organic Chemistry USSR (English Translation), 1983, p. 297 - 300[2] Zhurnal Organicheskoi Khimii, 1983, vol. 19, # 2, p. 339 - 343
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Reference:
[1] Canadian Journal of Chemistry, 1987, vol. 65, p. 2428 - 2433
With nitric acid; In acetic acid; at 15 - 20℃; for 1h;
General procedure: Compound 1a-1e or 1p-1s, 15 g, was dispersed in25 mL of glacial acetic acid, and 10 equiv of fuming nitric acid was added dropwise with stirring at 15-20C. The mixture was stirred for 1 h at 20C, and a solution of 5 g of urea in 120 mL of 15% aqueous acetic acid was slowly added dropwise with vigorous stirring, maintaining the temperature no higher than25C. The mixture was then slowly heated to 100C,kept for 1 h at that temperature, and cooled to 50C,and 40% aqueous sodium hydroxide was added to pH 10. The mixture was cooled to room temperature,and the precipitate was filtered off and recrystallized.
Example 49 The reaction was effected in the same manner as Example 44 except for using <strong>[768-91-2]1-<strong>[768-91-2]methyladamantane</strong></strong> instead of adamantane. The conversion of <strong>[768-91-2]1-<strong>[768-91-2]methyladamantane</strong></strong> was 71%, and 1-carboxy-3-<strong>[768-91-2]methyladamantane</strong> (yield 66%) was formed.
Direct Amide Formation of <strong>[768-91-2]1-<strong>[768-91-2]methyladamantane</strong></strong> with Formamide 1 mL technical grade nitric acid (65%) is added to 1.5026 g (10 mmol) <strong>[768-91-2]1-<strong>[768-91-2]methyladamantane</strong></strong>, while cooling to 0 C. in a heated 100 mL round bottom flask with an active magnetic stirrer. Subsequently, 25 mL technical grade sulfuric acid (95-98%) are added dropwise at 0 C. within 3 hours. One stirs for 12 h at 0 C. and further 10 mL 95-98% sulfuric acid are added. After 3 further hours of stirring at 0 C., the resulting solution is added dropwise to 50 mL technical grade formamide, within one hour of intensive stirring under exclusion of moisture at 0 C. This mixture is then stirred again for 30 min at 0 C. and 120 min at room temperature, after which at first 100 mL dichloromethane are added. The phases are separated, the aqueous phase is extracted with dichloromethane (2×20 mL), and the combined organic phases are driedNa2SO4. After the desiccant has been filtered off, the solvents are largely removed from the solution by rotary evaporation. The remaining yellowish crude product is purified by column chromatography (170 g SiO2, acetic acid ethyl ester, Rf=0.37). After careful evaporation of the eluent, one obtains 0.864 g (45%) 1-formamido-3-<strong>[768-91-2]methyladamantane</strong> as weakly yellowish, viscose oil, crystallizing into colorless needles during prolonged standing.1H NMR (200 MHz, CDCl3): delta/ppm=8.25 (d, J=12.4 Hz) and 8.05 (d, J=9.0 Hz), together 1H, NHCHO (2 isomers); 6.62 (bs) and 5.33 (bs), together 1H, NHCHO (2 isomers); 2.22-1.33 (m, 14H, CH/CH2 of the adamantane); 0.87 (s) and 0.85 (s), together 3H, -CH3 (2 isomers).13C NMR (50 MHz, CDCl3): delta/ppm=162.6 and 160.4 (CO), 53.0 and 51.6, 50.7 and 48.4, 43.3 and 43.2, 42.9 and 41.1, 35.5 and 35.1, 32.0 and 31.9, 30.4 and 30.3, 29.7 and 29.6 (signals doubled, as there are two isomers).IR (KBr): {tilde(nu)}/cm-1=3439, 3211, 3083, 2902, 2849, 1696, 1675, 1536, 1456, 1313.MS: m/z=193 (M+), 178, 148, 136, 122, 106, 92, 79