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	US06667300B2
Source dataset	uspto-grants-2003_12
ORD ID	ord-72691081d87c4372bf34488573d4395b
Source note	uspto-grants-2003_12