HCID 178418361, compound → HCID 178515274, compound

HRID 567707Notes

Reaction equation

HRID 567707 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:20](=[O:21])[C:11]3=[N:12][NH:13][C:14]4[CH:15]=[CH:16][CH:17]=[CH:18][C:19]=4[C:10]3=[N:9]2)=[CH:4][CH:3]=1.[H][H]>FC(F)(F)C(O)=O.[Pt]=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:20](=[O:21])[C:11]3=[N:12][NH:13][C:14]4[CH2:15][CH2:16][CH2:17][CH2:18][C:19]=4[C:10]3=[N:9]2)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 178418361HCID 178418361, compoundHCID 178515276HCID 178515276, compound

Product 1

HCID 178515274HCID 178515274, compound

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 6422Trifluoroacetic acidSolvent

Procedure

To 2-(4-chlorophenyl)-2,5-dihydropyrazolo[4,3-c]cinnolin-3-one (0.5 g) dissolved in trifluoroacetic acid (20 ml) was added platinum oxide (0.2 g). The re action mixture was hydrogenated at 50 psi until no further uptake of hydrogen was observed. The catalyst was collected by filtration, the filtrate was poured onto ice and basified with ammonia. On the addition of dichloromethane a solid precipitated out; the solid was collected by filtration, washed with water and dried. Recrystallisation from ethanol gave the title compound. δH (360 MHz; DMSO-d6) 1.83 (4H, m, CH2), 2.67 (2H, t, J=5.7 Hz, CH2), 2.75 (2H, t, J=5.7 Hz, CH2), 7.51 (2H, d, J=9 Hz, ArH), 8.23 (2H, d, J=9 Hz, ArH), m/z (ESP+) 301/303 (MH+).

Workup

  1. filtrationThe catalyst was collected by filtration
  2. additionthe filtrate was poured onto ice
  3. additionOn the addition of dichloromethane a solid
  4. customprecipitated out
  5. filtrationthe solid was collected by filtration
  6. washwashed with water
  7. customdried
  8. customRecrystallisation from ethanol

Sources & evidence

ORD record
ord-35eab3372e8e447fb1feb2d307a789b0
Source dataset
uspto-grants-2001_01
Patent number
US06180630B2

Reaction notes

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