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

HRID 467907Notes

Reaction equation

HRID 467907 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-17baf1b4ba774dc6a4f84c8a8ca6994b
Source dataset
uspto-grants-2014_01
Patent number
US08623881B2

Reaction notes

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