N,N-Dimethylethylenediamine → 9-Chloro-6-[(2-dimethylaminoethyl)amino]-4-(p-methoxybenzyloxy)benzo[g]isoquinoline-5,10-dione

HRID 234828Notes

Reaction equation

HRID 234828 reaction equation
[CH3:1][N:2]([CH3:6])[CH2:3][CH2:4][NH2:5].[Cl:7][C:8]1[C:21]2[C:20](=[O:22])[C:19]3[CH:18]=[N:17][CH:16]=[C:15]([O:23][CH2:24][C:25]4[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=4)[C:14]=3[C:13](=[O:33])[C:12]=2[C:11](F)=[CH:10][CH:9]=1>N1C=CC=CC=1>[Cl:7][C:8]1[C:21]2[C:20](=[O:22])[C:19]3[CH:18]=[N:17][CH:16]=[C:15]([O:23][CH2:24][C:25]4[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=4)[C:14]=3[C:13](=[O:33])[C:12]=2[C:11]([NH:5][CH2:4][CH2:3][N:2]([CH3:6])[CH3:1])=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 66053N,N-DimethylethylenediamineHCID 153619409-Chloro-6-fluoro-4-(p-methoxy benzyloxy)benzo[g]isoquinoline-5,10-dione

Product 1

HCID 540214979-Chloro-6-[(2-dimethylaminoethyl)amino]-4-(p-methoxybenzyloxy)benzo[g]isoquinoline-5,10-dione

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A pyridine solution (0.4 mL) of N, N-dimethylethylenediamine (0.049 g) is added to 9-chloro-6-fluoro-4-(p-methoxybenzyloxy)benzo[g ]isoquinoline-5,10-dione of Preparative Example 29 (0.011 g) and the resultant solution is stirred under a nitrogen atmosphere for 1.75 h at room temperature. The excess amine and pyridine are removed under a slow stream of nitrogen. The residue is placed under vacuun for 3 h and purified by silica gel column chromathography commencing with 1% to 2% methanol in dichloromethane. The removal of the eluents yields 9-chloro-6-[(2-dimethylaminoethyl)amino]-4-(p-methoxybenzyloxy)benzo[g]isoquinoline-5,10-dione as a purple solid (10 mg).

Workup

  1. customThe excess amine and pyridine are removed under a slow stream of nitrogen
  2. custompurified by silica gel column chromathography
  3. customThe removal of the eluents

Sources & evidence

ORD record
ord-b6a015fddc9442608731b588ad1ca4a0
Source dataset
uspto-grants-1997_01
Patent number
US05596097

Reaction notes

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