HCID 178418361, compound → HCID 178507347, compound

HRID 1907221Notes

Reaction equation

HRID 1907221 reaction equation
[N+:1]([C:4]1[CH:13]=[CH:12][C:11]2[NH:10][CH:9]=[C:8]3[C:14](=[O:23])[N:15]([C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=4)[N:16]=[C:7]3[C:6]=2[CH:5]=1)([O-])=O.[H][H]>CO.[Pd]>[NH2:1][C:4]1[CH:13]=[CH:12][C:11]2[NH:10][CH:9]=[C:8]3[C:14](=[O:23])[N:15]([C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=4)[N:16]=[C:7]3[C:6]=2[CH:5]=1

Participants

5

Reactant 2

HCID 178418361HCID 178418361, compoundHCID 178515216HCID 178515216, compound

Product 1

HCID 178507347HCID 178507347, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 5a in methanol were added catalytic amounts of Pd on carbon. Reaction mixture was stirred at 20 psi of hydrogen overnight. Solid was filtered off and methanol was removed in vacuo to afford 8-amino-2-phenyl-2,5-dihydro-pyrazolo-(4,3-c) quinolin-3-one in 87% yield. 1H-NMR (DMSO-d6) δ (ppm): 6.92 (1H, dd, J=8.79, 2.47 Hz), 7.13 (1H, m), 7.28 (1H, d, J=2.47 Hz), 7.43 (3H, m), 8.20 (2H, dd, J=7.69, 1.10 Hz), 8.44 (1H, d, J=6.59 Hz). m/z 277.3 (MH+).

Workup

  1. customReaction mixture
  2. filtrationSolid was filtered off
  3. custommethanol was removed in vacuo

Sources & evidence

ORD record
ord-2ee4e6fcee0c40318b3c188e7597515d
Source dataset
uspto-grants-2013_12
Patent number
US08598159B2

Reaction notes

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