1-benzoyl-1,2,3,4-tetrahydroquinolin-6-amine synthesis

9synthesis methods

Product Name:1-benzoyl-1,2,3,4-tetrahydroquinolin-6-amine
CAS Number:857759-22-9
Molecular formula:C16H16N2O
Molecular Weight:252.31

Methanone, (3,4-dihydro-6-nitro-1(2H)-quinolinyl)phenyl-

30450-57-8
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1-benzoyl-1,2,3,4-tetrahydroquinolin-6-amine

857759-22-9
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Yield:857759-22-9 79%

Reaction Conditions:

with ammonium chloride;zinc in methanol;water at 60; for 6 h;

Steps:

5.7. Synthesis of (6-amino-3,4-dihydroquinolin-1(2H)-yl)(4-chlorophenyl)methanone (8a):

General procedure: The mixture of ammonium chloride (7000 mmol, 0.5 gm) was preparedin water: methanol (3:7). Simultaneously the compound 7a (1000mmol, 0.3 gm) was added to suitable quantity of methanol followed bythe addition of the zinc dust (10000 mmol, 0.43 gm). The above mixtureof ammonium chloride was poured into this reaction mixture of compoundand zinc dust. This reaction mixture was allowed to stir at 60 Cfor 6 h resulted into the reduction of nitro group to amine. Furthermethanol was evaporated and the mixture was dissolved in the ethylacetate and extracted with bicarbonate. The compound was dried overthe sodium sulfate. Yield: 80%; mp: 190-193 C; IR (KBr, γmax cm 1):1552(C- -O), 1600(C- -C), 2360(C-N), 2931(C-H aliphatic), 3361(C-H aromatic); MS (EI) m/z calculated for C16H15ClN2O 287 (M + 1),found 287.5 (M + 1) and 289.5 for chloro pattern.

References:

Chaube, Udit J.;Rawal, Rakesh;Jha, Abhishek B.;Variya, Bhavesh;Bhatt, Hardik G. [Bioorganic Chemistry,2021,vol. 106]