O-Toluidine → HCID 178486494, compound

HRID 2213710Notes

Reaction equation

HRID 2213710 reaction equation
[CH3:1][C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[NH2:4].Cl[C:10]1[CH:27]=[C:14]2[C:15]3[C:20]([CH2:21][CH2:22][N:13]2[C:12](=[O:28])[N:11]=1)=[CH:19][C:18]([O:23][CH3:24])=[C:17]([O:25][CH3:26])[CH:16]=3>CC(O)C>[CH3:24][O:23][C:18]1[CH:19]=[C:20]2[C:15](=[CH:16][C:17]=1[O:25][CH3:26])[C:14]1=[CH:27][C:10](=[N:4][C:3]3[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=3[CH3:1])[NH:11][C:12](=[O:28])[N:13]1[CH2:22][CH2:21]2

Participants

4

Reactant 2

HCID 7242O-ToluidineHCID 46787202-Chloro-6,7-dihydro-9,10-dimethoxy-4H-pyrimido[6,1-a]isoquinolin-4-one

Product 1

HCID 178486494HCID 178486494, compoundYield 100.4%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

2-Methylaniline (5.44 ml, 51 mmol) and 2-chloro-9,10-dimethoxy-6,7-dihydro-4H-pyrimido[6,1-a]isoquinolin-4-one (5 g, 17 mmol) were suspended in propan-2-ol (400 ml) and heated at reflux, under nitrogen, for 24 h After cooling to room temperature, the solution was concentrated in vacuo and the residue purified by flash column chromatography [dichloromethane/methanol (98:2–96:4)] to afford the title compound (6.2 g, quantitative yield) as a yellow/orange solid.

Workup

  1. temperatureheated
  2. temperatureat reflux, under nitrogen, for 24 h
  3. concentrationthe solution was concentrated in vacuo
  4. customthe residue purified by flash column chromatography [dichloromethane/methanol (98:2–96:4)]

Sources & evidence

ORD record
ord-3e78a0544bde46fd981e021ad5700f78
Source dataset
uspto-grants-2006_09
Patent number
US07105663B2

Reaction notes

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