Toluene → ethyl 6-({2-[2-(dimethylamino)ethyl]-1,3-dioxo-2,3-dihydro-1H-dibenzo[de,h]isoquinolin-11-yl}amino)-4,6-dioxohexanoate

HRID 18137Notes

Reaction equation

HRID 18137 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.C1(C)C=CC=CC=1.CC1(C)OC(=O)[C:37](=[C:41]([OH:49])[CH2:42][CH2:43][C:44]([O:46][CH2:47][CH3:48])=[O:45])[C:36](=O)[O:35]1>C(Cl)Cl.CO>[CH3:21][N:19]([CH3:20])[CH2:18][CH2:17][N:12]1[C:11](=[O:22])[C:10]2[CH:23]=[CH:24][CH:25]=[C:8]3[C:9]=2[C:14](=[C:15]2[C:2]([NH:1][C:36](=[O:35])[CH2:37][C:41](=[O:49])[CH2:42][CH2:43][C:44]([O:46][CH2:47][CH3:48])=[O:45])=[CH:3][CH:4]=[CH:5][C:6]2=[CH:7]3)[C:13]1=[O:16]

Participants

5

Reactant 3

HCID 1140TolueneHCID 1006541311-amino-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dioneHCID 59549553Ethyl 4-(2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-ylidene)-4-hydroxybutanoate

Product 1

HCID 16717934ethyl 6-({2-[2-(dimethylamino)ethyl]-1,3-dioxo-2,3-dihydro-1H-dibenzo[de,h]isoquinolin-11-yl}amino)-4,6-dioxohexanoateYield 37.1%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

100 mg of 11-amino-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione (obtained in example 3) (0.30 mmol), 7 mL of toluene and 70 mg of ethyl 4-(2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-ylidene)-4-hydroxybutanoate (1.1 molar equivalent) were refluxed for 6 hours. After cooling, the solvent was 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 48 mg yield=29% of the desired product (formula below) as a red powder.

Workup

  1. temperatureAfter cooling
  2. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-864179d320484d5694601d1c85ce41ea
Source dataset
uspto-grants-2010_06
Patent number
US07741337B2

Reaction notes

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