These common heterocyclic compound, 24566-80-1, name is 2-(10-Bromodecyl)isoindoline-1,3-dione, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. Safety of 2-(10-Bromodecyl)isoindoline-1,3-dione
A mixture of secondary amine from intermediate 1 C (3,6 g, 1 5 ,8 mmol), N-i I 0- ba>mod.ecyl)phthaUmide (4.4 g, 12.0 mmol), (2.0 g, 12.4 mmol) and 2CO3 (8.2 g. 59,4 ramol) in aeetomtrile (90 mL) was stirred at reflux overnight. After filtration, volatile components were evaporated in vacuo. The resulting residue was purified by silica gel column chromatography (5% methanol in dichloromethane) to give the desired phthaltmido- protected i termediate 5b (6.0 g, 86% yield) as a Sight, brown oil, (0272) [0170] Compound 5b (2,9 g, 4.9 mmol) was refluxed with hydrazine hydrate (700 rag, 13.9 mmol in ethanol ( 100 mi.,) for 5 h. The solvent was evaporated and 10% aqueous solution of aOH {20 ml.) was added. The mixture was extracted with CH2CI2. dried over NasSO-t. and evaporated to give the primary amine ;V-(9-( 10-a.minodecy})-9~ (0273) azabkyco[3,3..1 “]nonan-3 -yl)-N -(2-methoxy-5-meihyiphenyl) carbamate 6b (2,2 g, 95% yield) as a Sight yellow oil. NMR (CDC ) 3 7.96 (s, 1H)S 7.14 (s, Eta), 6.72-6,80 (m, 2H), 5.10-5. J 8 (m, 1 H 3.84 (s, 3fl), 3.04-3.07 (m, 2H), 2.65-2.70 (m, 2H), 2.53-2.58 (ra, 2H), 2.39-2.49 (m, 2H), 2.29 (s, 3H>, 2.08-2.20 (in, 1 B), 1 .83- i .94 (ra 2.W). 1.18-1.54 (ra, 23H).
The synthetic route of 2-(10-Bromodecyl)isoindoline-1,3-dione has been constantly updated, and we look forward to future research findings.
Reference:
Patent; WASHINGTON UNIVERSITY; HAWKINS, William; MACH, Robert; SPITZER, Dirk; VANGVERAVONG, Suwanna; (84 pag.)WO2015/153814; (2015); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem