Potassium Bromide → 8,9-Dimethoxy-2,3-methylenedioxy-5-[2-(N,N-dimethylamino)-1-methylethyl]-5H-dibenzo [c,h]1,6-naphthyridin-6-one

Participants

Role	Name	HCID	Charge
Reactant	Potassium Bromide	HCID 253877	—
Reactant	N-(6,7-Methylenedioxyquinolin-4-yl)-N-[2-(N,N-dimethylamino)--methylethyl)-2-iodo-4,5-dimethoxybenzamide	HCID 22139524	—
Product	8,9-Dimethoxy-2,3-methylenedioxy-5-[2-(N,N-dimethylamino)-1-methylethyl]-5H-dibenzo [c,h]1,6-naphthyridin-6-one	HCID 22139491	30.4%

Reaction Steps

Prepared from N-(6,7-Methylenedioxyquinolin-4-yl)-N-[2-(N,N-dimethylamino)-1-methylethyl)-2-iodo-4,5-dimethoxybenzamide; (30.4% yield); reaction time 30 min; mp 186-187° C.; IR (KBr) 1649; 1H NMR (CDCl3); δ 1.95-1.98 (m, 9H), 2.77 (dd, 1H, J=12.0, 8.0), 3.21 (dd, 1H, J=12.0, 8.0), 4.06 (s, 3H), 4.13 (s, 3H), 4.84-4.92 (m, 1H), 6.17 (s, 2H), 7.46 (s, 1H), 7.66 (s, 1H), 7.77 (s, 1H), 7.87 (s, 1H), 9.35 (s, 1H); 13C NMR (CDCl3) δ 19.7, 45.5, 56.2, 56.3, 59.5, 63.1, 100.9, 101.9, 102.1, 107.0, 108.7, 112.4, 115.2, 120.5, 127.3, 142.6, 143.3, 147.0, 147.3, 149.9, 150.1, 154.0, 164.9; HRMS calcd for C24H25N3O5H: 436.1794; found 436.1863.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07049315B2
Source dataset	uspto-grants-2006_05
ORD ID	ord-a29e9e3a43f24325951c78262318139d
Source note	uspto-grants-2006_05