4-Chlorophenylacetyl chloride → 2-(4-chlorophenyl)-N-{2-[2-(dimethylamino)ethyl]-1,3-dioxo-2,3-dihydro-1H-dibenzo[de,h]isoquinolin-11-yl}acetamide

HRID 18129

Reaction equation

HRID 18129 reaction equation
[NH2:1][C:2]1[C:15]2[C:6](=[CH:7][C:8]3[C:9]4[C:14]=2[C:13](=[O:16])[N:12]([CH2:17][CH2:18][N:19]([CH3:21])[CH3:20])[C:11](=[O:22])[C:10]=4[CH:23]=[CH:24][CH:25]=3)[CH:5]=[CH:4][CH:3]=1.[Cl:26][C:27]1[CH:32]=[CH:31][C:30]([CH2:33][C:34](Cl)=[O:35])=[CH:29][CH:28]=1>ClCCl>[Cl:26][C:27]1[CH:32]=[CH:31][C:30]([CH2:33][C:34]([NH:1][C:2]2[C:15]3[C:6](=[CH:7][C:8]4[C:9]5[C:14]=3[C:13](=[O:16])[N:12]([CH2:17][CH2:18][N:19]([CH3:20])[CH3:21])[C:11](=[O:22])[C:10]=5[CH:23]=[CH:24][CH:25]=4)[CH:5]=[CH:4][CH:3]=2)=[O:35])=[CH:29][CH:28]=1

Participants

4

Reactant 2

HCID 906924-Chlorophenylacetyl chlorideHCID 1006541311-amino-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione

Product 1

HCID 167178402-(4-chlorophenyl)-N-{2-[2-(dimethylamino)ethyl]-1,3-dioxo-2,3-dihydro-1H-dibenzo[de,h]isoquinolin-11-yl}acetamideYield 84%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 100 mg (0.30 mmole) of 11-amino-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione (obtained in example 3) in 7 mL of dichloromethane was magnetically stirred at 20° C. 113 μL (2 molar equivalents) of 4-chlorophenylacetyl chloride were added. The mixture was magnetically stirred at room temperature during 3 hours. The solvent was then evaporated under reduced pressure and the residue was submitted to a flash chromatography on silica (eluent: CH2Cl2/methanol in a 97:3 volume ratio) to provide 122 mg (yield: 84%). of the desired product (formula above) as an orange powder which was characterized as follows:

Workup

  1. customThe solvent was then evaporated under reduced pressure
  2. customCH2Cl2/methanol in a 97:3 volume ratio) to provide 122 mg (yield: 84%)

Sources & evidence

ORD record
ord-de30689099b04dcc8fd2962cf92b9651
Source dataset
uspto-grants-2010_06
Patent number
US07741337B2

Linked notes

Loading…