Chloroacetyl chloride → 2-Chloromethyl-3-(2-chlorophenyl)-3H-benzo[g]quinazolin-4-one

Participants

Role	Name	HCID	Charge
Reactant	Chloroacetyl chloride	HCID 6577	—
Reactant	3-Aminonaphthalene-2-carboxylic acid (2-chlorophen-yl)amide	HCID 61209521	—
Solvent	Acetic Acid	HCID 176	—
Product	2-Chloromethyl-3-(2-chlorophenyl)-3H-benzo[g]quinazolin-4-one	HCID 22316583	39%

Reaction Steps

Prepared according to Procedure B with 1n (500 mg, 1.68 mmol) and chloroacetyl chloride (0.40 mL, 5.05 mmol) in acetic acid (10 mL). Purified by chromatography in CH2Cl2 followed by recrystallization from isopropanol to afford 232 mg of a light-brown solid (39%). 1H NMR (CDCl3) δ: 8.92 (s, 1H); 8.29 (s, 1H); 8.81 (d, J=8.3, 1H); 8.32 (d, J=8.3 Hz, 1H); 7.51-7.69 (m, 4H); 7.55 (d, J=5.2 Hz, 1H); 7.53 (d, J=3.8 Hz, 1H); 4.43 (d, J=12 Hz, 1H), 4.12 (d, J=12 Hz, 1H). MS (ES): m/z 355.0 (M+).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08637533B2
Source dataset	uspto-grants-2014_01
ORD ID	ord-7ba3dd5316e24a338328e45e05c1a36f
Source note	uspto-grants-2014_01