N,N-Dimethylethylenediamine → 5-[[2-(dimethylamino)ethyl]amino]-2-methylisoquino[5,6,7-cd]indazole-6(2H)-one

HRID 234832Notes

Reaction equation

HRID 234832 reaction equation
Cl[C:2]1[CH:10]=[CH:9][C:8]2[N:7]([CH3:11])[N:6]=[C:5]3[C:12]4[CH:13]=[CH:14][N:15]=[CH:16][C:17]=4[C:18](=[O:19])[C:3]=1[C:4]=23.[CH3:20][N:21]([CH3:25])[CH2:22][CH2:23][NH2:24]>>[CH3:20][N:21]([CH3:25])[CH2:22][CH2:23][NH:24][C:2]1[CH:10]=[CH:9][C:8]2[N:7]([CH3:11])[N:6]=[C:5]3[C:12]4[CH:13]=[CH:14][N:15]=[CH:16][C:17]=4[C:18](=[O:19])[C:3]=1[C:4]=23

Participants

3

Reactant 2

HCID 66053N,N-DimethylethylenediamineHCID 199747705-chloro-2-methylisoquino[5,6,7-cd]indazole-6(2H)-one

Product 1

HCID 199747415-[[2-(dimethylamino)ethyl]amino]-2-methylisoquino[5,6,7-cd]indazole-6(2H)-one

Procedure

5-chloro-2-methylisoquino[5,6,7-cd]indazole-6 (2H)-one of Example 7 (0.013 g) is added to 2-(dimethylamino)ethylamine (0.34 mL). The yellow mixture is heated quickly to reflux for 1 hour. The excess diamine is removed from the orange solution by a gentle stream of nitrogen. The orange mixture obtained is purified by silica gel column chromatography with a gradient elution (1% methanol/chloroform (25 mL), 2% methanol/chloroform (25 mL), 4% methanol/chloroform (25 mL), 8% methanol/chloroform (25 mL), 12% methanol/chloroform (25 mL), 16% methanol/chloroform (25 mL), 24% methanol/chloroform (50 mL)) to yield 5-[[2-(dimethylamino)ethyl]amino]-2-methylisoquino[5,6,7-cd]indazole-6(2H)-one (0.010 g) as a reddish orange solid.

Workup

  1. temperatureThe yellow mixture is heated quickly
  2. temperatureto reflux for 1 hour
  3. customThe excess diamine is removed from the orange solution by a gentle stream of nitrogen
  4. customThe orange mixture obtained
  5. customis purified by silica gel column chromatography with a gradient elution (1% methanol/chloroform (25 mL), 2% methanol/chloroform (25 mL), 4% methanol/chloroform (25 mL), 8% methanol/chloroform (25 mL), 12% methanol/chloroform (25 mL), 16% methanol/chloroform (25 mL), 24% methanol/chloroform (50 mL))

Sources & evidence

ORD record
ord-1c9dcf740d32406b9c542abbe30ce882
Source dataset
uspto-grants-1997_01
Patent number
US05596097

Reaction notes

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