Water → HCID 178524940, compound

HRID 1760179Notes

Reaction equation

HRID 1760179 reaction equation
[Mn]([O-])(=O)(=O)=[O:2].[K+].[C:7]1([C:13]2[C:22]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[C:16]3[NH:23][N:24]=[C:25]([CH3:26])[C:15]=3[N:14]=2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[OH2:27]>N1C=CC=CC=1>[C:7]1([C:13]2[C:22]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[C:16]3[NH:23][N:24]=[C:25]([C:26]([OH:2])=[O:27])[C:15]=3[N:14]=2)[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 962WaterHCID 516875Potassium PermanganateHCID 178434201HCID 178434201, compound

Product 1

HCID 178524940HCID 178524940, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
40 °C

Procedure

2.1 g of potassium permanganate in 36 ml of water were added to a solution of 600 mg of 5-phenyl-3-methyl-1H-pyrazolo[4,3-c]isoquinoline in 36 ml of pyridine. The mixture was stirred at 40° C. for 12 h. The resulting suspension was filtered with suction through silica gel, after which the filtrate was concentrated under reduced pressure and the residue was purified by means of HPLC (Merk-Hibar-Lichrospher 100-RP-18, water (0.1% trifluoroacetic acid)/acetonitrile (0.1% trifluoroacetic acid)=80/20→10/90). The following was obtained: 60. C17H11N3O2 (289.30) MS (ESI) 290 (M+H)

Workup

  1. filtrationThe resulting suspension was filtered with suction through silica gel
  2. concentrationafter which the filtrate was concentrated under reduced pressure
  3. customthe residue was purified by means of HPLC (Merk-Hibar-Lichrospher 100-RP-18, water (0.1% trifluoroacetic acid)/acetonitrile (0.1% trifluoroacetic acid)=80/20→10/90)
  4. customThe following was obtained

Sources & evidence

ORD record
ord-3dddb386cedd4c808217bf94da83423d
Source dataset
uspto-grants-2005_01
Patent number
US06841556B2

Reaction notes

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