6-Amino-3,4-dihydroquinolin-2(1H)-one
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6-Amino-3,4-dihydroquinolin-2(1H)-one
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CAS No:
22246-13-5
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Formula:
C9H10N2O
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Chemical Name:
6-Amino-3,4-dihydroquinolin-2(1H)-one
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Synonyms:
2(1H)-Quinolinone,6-amino-3,4-dihydro-;Carbostyril,6-amino-3,4-dihydro-;6-Amino-3,4-dihydro-2(1H)-quinolinone;6-Amino-3,4-dihydrocarbostyril;6-Amino-1,3,4-trihydroquinolin-2-one;6-Amino-3,4-dihydro-1H-quinolin-2-one;6-Amino-3,4-dihydroquinolin-2(1H)-one;6-Amino-3,4-dihydroquinoline-2(1H)-one
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CAS No:
Safety Information
|Warning|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P312, P304+P340, P305+P351+P338, P312, P321, P322, P330, P332+P313, P337+P313, P362, P363, 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-Amino-3,4-dihydroquinolin-2(1H)-one Use and Manufacturing
To a solution of 6-nitro-3, 4-dihydroquinolin-2(lH)-one (3 g) in MeOH (60 mL) at 0°C, Zn dust (5 eq) and ammonium chloride (5 eq) were added portion wise and the mixture stirred at rt for 1 h while monitoring by TLC. After completion, the mixture was filtered over Celite® bed and resulting filtrate concentrated. The residue was diluted with 5percent MeOH in DCM and washed with water. The organic layer was dried over sodium sulfate, filtered and concentrated to obtain 6-amino-3, 4-dihydroquinolin-2(lH)-one (2.3 g, 91percent). 1H NMR (DMSO-dTo a suspension of l, 2-dihydro-6-nitroisoquinolin-3(4H)-one (10.3 g, 53.6 mmol) in MeOH (150 mL) was added 10percent Pd/C (1.14 g, 1.07 mmol) and the mixture was stirred overnight under H6-Nitro-3, 4- dihydroquinolin-2(lH)-one (1.0 g, 5.2 mmol) was dissolved in 40 mL of EtOH, and then H4CI (2.76 g, 52 mmol) in 20 mL of H2O and Zn dust (2.37 g, 36.4 mmol) were added. After refluxing at 80 °C for 1 h, the mixture was filtered to remove Zn dust. The filtration was concentrated to give the desired product (1.8 g, including partial H4CI) as a gray solid. NMR (300 MHz, DMSO-^e) δ 9.67 (s, 1H), 6.55 (d, J = 8.2 Hz, 1H), 6.42 - 6.31 (m, 2H), 2.70 (t, J= 7.5 Hz, 2H), 2.33 (dd, J= 8.5 Hz, 6.5 Hz, 2H).
Computed Properties
Molecular Weight:162.19
XLogP3:0.4
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:2
Exact Mass:162.079312947
Monoisotopic Mass:162.079312947
Topological Polar Surface Area:55.1
Heavy Atom Count:12
Complexity:193
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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6-Amino-3,4-dihydroquinolin-2(1H)-one
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