6-Aminomethylquinoline
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6-Aminomethylquinoline
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CAS No:
99071-54-2
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Formula:
C10H10N2
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Chemical Name:
6-Aminomethylquinoline
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Synonyms:
6-AMINOMETHYLQUINOLINE;ART-CHEM-BB B016095;6-Quinolinemethanamine;QUINOLINE-6-YLMETHANAMINE;6-Methylaminoquinoline;(quinolin-6-ylmethyl)amine;1-quinolin-6-ylmethanamine;(quinolin-6-ylmethyl)amine(SALTDATA: 2HCl)
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CAS No:
Safety Information
IRRITANT
|Danger|H302 (50%): Harmful if swallowed [Warning Acute toxicity, oral]|P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P310, P312, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 2 companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
6-Aminomethylquinoline Use and Manufacturing
Step 5:To a solution of quinoline-6-carbonitrile (96 g, 0.62 mol) in saturated ammonia in methanol (1 lit.), Raney-Ni (10 g) was added and the mixture was stirred at 1 atm of HStep 5: Quinolin-6-ylmefhanamine: To a solution of quinoline-6-carbonitrile (96 g, 0.62 mol) in saturated ammonia in methanol (1 lit.), Raney-Ni (lOg) was added and the mixture was stirred at 1 atm of HStep 5: The intermediateA-2 (4.7 g, 30.5 mmol) was dissolvedin NH6-Cyanoquinoline A-2 (4.7 g, 30 mmol) was dissolved in a methanolic ammonia solution (7 mol / L, 50 mL) Hydrogenation reduction was performed using a hydrogenation instrument H-cube (30 bar, 25 ° C, flow rate 1 mL / min, Raney Ni) The crude product was obtained and isolated in reverse phase to give 3.8 g of quinoline-6-methyleneamine A, yield: 79percentQuinolin-6-ylmethanamine (intermediate D) To a solution of 2-(quinolin-6-ylmethyl)isoindoline-1 , 3-dione (2Og, 69.4 mmol) in MeOH (100 mL), was added hydrazine hydrate (3.47 g, 69.4 mmol). The solution was heated to reflux for 3h, then cooled to rt, filtered through celite. The filtrate was concentrated in vacuo and EtOAc was added to dilute the residue, filtered and concentrated in vacuo to afford 6-bromo- N2-(quinolin-6-ylmethyl)pyrazine-2, 3-diamine (5g) in 41 percent yield 41 percent. LCMS (method B): [MH]To a solution of 2-(quinolin-6-ylmethyl)isoindoline-1 , 3-dione (2Og, 69.4 mmol) in MeOH (100 mL) was added hydrazine monohydrate (3.47 g, 69.4 mmol). The solution was heated at reflux for 3 h, then cooled to rt and filtered through celite. The filtrate was concentrated in vacuo. EtOAc then was added to the residue and the resulting solution was filtered and concentrated in vacuo to afford 5 g (41 percent) of the title compound. LCMS (method B): [MH]
Computed Properties
Molecular Weight:158.20
XLogP3:1.1
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:1
Exact Mass:158.084398327
Monoisotopic Mass:158.084398327
Topological Polar Surface Area:38.9
Heavy Atom Count:12
Complexity:147
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes