6-BroMo-3-iodo-1H-quinolin-4-one synthesis

3synthesis methods

Product Name:6-BroMo-3-iodo-1H-quinolin-4-one
CAS Number:1320361-71-4
Molecular formula:C9H5BrINO
Molecular Weight:349.95

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1320361-71-4
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Yield:1320361-71-4 93%

Reaction Conditions:

with N-iodo-succinimide in N,N-dimethyl-formamide at 20; for 0.05 h;

Steps:

6-Bromo-3-iodoquinolin-4(1H)-one (2).

N-iodosuccinimide (3 g, 13.4 mmol) was added to a solution of 3 (2 g, 8.92 mmol) in dry DMF (27 mL) maintained under stirring at room temperature. After 3 min, the mixture was diluted with water and the precipitate which formed was filtered and washed with water and diethyl ether to afford 2 (2.9 g, 93%) as a withe solid. R_f 0.72 (CH₂Cl₂/MeOH, 9/1); mp >290 °C; ¹H NMR (200 MHz, (CD₃)₂SO): δ 12.27 (s, 1H), 8.47 (s, 1H), 8.10 (d, J = 2.4 Hz, 1 H), 7.79 (dd, J_ortho = 9.0 Hz, J_meta = 2.4 Hz, 1H), 7.47 (d, J = 8.9 Hz, 1H); ¹³C NMR (100 MHz, (CD₃)₂SO) δ 172.4, 145.6, 138.9, 135.1, 128.0, 124.1, 121.6, 117.0, 81.3; IR (Nujol): n = 1614 cm^-1; MS: m/z (M⁺ + 1) = 350.

References:

Mugnaini, Claudia;Falciani, Chiara;De Rosa, Maria;Brizzi, Antonella;Pasquini, Serena;Corelli, Federico [Tetrahedron,2011,vol. 67,# 32,p. 5776 - 5783] Location in patent:supporting information; experimental part

2-Propenoic acid, 3-[(4-bromophenyl)amino]-, ethyl ester

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1320361-71-4
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References

106-40-1 Synthesis

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1320361-71-4
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References