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

HRID 497109Notes

Reaction equation

HRID 497109 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]([C:11]1[C:20]([NH2:21])=[CH:19][C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=1)=[O:10].[Cl:22][CH2:23][C:24](Cl)=O>C(O)(=O)C>[Cl:22][CH2:23][C:24]1[N:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[Cl:1])[C:9](=[O:10])[C:11]2[C:20](=[CH:19][C:18]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[CH:12]=2)[N:21]=1

Participants

4

Reactant 2

HCID 6577Chloroacetyl chlorideHCID 612095213-Aminonaphthalene-2-carboxylic acid (2-chlorophen-yl)amide

Product 1

HCID 223165832-Chloromethyl-3-(2-chlorophenyl)-3H-benzo[g]quinazolin-4-oneYield 39%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

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+).

Workup

  1. customPrepared
  2. customPurified by chromatography in CH2Cl2
  3. customfollowed by recrystallization from isopropanol

Sources & evidence

ORD record
ord-3983ad591012461fadd977b468a8131f
Source dataset
uspto-grants-2005_09
Patent number
US06949535B2

Reaction notes

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