Acetic Acid → HCID 178498107, compound

HRID 2243413Notes

Reaction equation

HRID 2243413 reaction equation
[CH3:1][O:2][C:3](=[O:33])[C:4]1[CH:9]=[CH:8][C:7]([N:10]2[C:31](=[O:32])[C:13]3=[C:14]([C:22]4[CH:27]=[CH:26][C:25]([N+:28]([O-])=O)=[CH:24][CH:23]=4)[NH:15][C:16]4[CH:17]=[CH:18][CH:19]=[CH:20][C:21]=4[C:12]3=[N:11]2)=[CH:6][CH:5]=1.C(O)(=O)C>C(O)C.CN(C=O)C.[Pd]>[CH3:1][O:2][C:3](=[O:33])[C:4]1[CH:9]=[CH:8][C:7]([N:10]2[C:31](=[O:32])[C:13]3=[C:14]([C:22]4[CH:27]=[CH:26][C:25]([NH2:28])=[CH:24][CH:23]=4)[NH:15][C:16]4[CH:17]=[CH:18][CH:19]=[CH:20][C:21]=4[C:12]3=[N:11]2)=[CH:6][CH:5]=1

Participants

6

Reactant 2

HCID 176Acetic AcidHCID 178498108HCID 178498108, compound

Product 1

HCID 178498107HCID 178498107, compoundYield 82.6%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 6228DimethylformamideSolvent

Procedure

4-[4-(4-Nitro-phenyl)-3-oxo-3,5-dihydro-pyrazolo[4,3-c]quinolin-2-yl]-benzoic acid methyl ester (2.6 g, 5.9 mmol) and Pd/C (100 mg, 10%) were suspended in ethanol (150 mL) and acetic acid (6 mL) and stirred under hydrogen for 24 h. The resulting yellow-orange suspension was diluted with DMF (50 mL) and filtered. The solvent was removed in vacuo to leave a residue which was washed with methanol to give 4-[4-(4-amino-phenyl)-3-oxo-3,5-dihydro-pyrazolo[4,3-c]quinolin-2-yl]-benzoic acid methyl ester (2.0 g, 82%) as a pale orange solid, LCMS m/z 411.39 [M+H]+ @ RT 1.27 min, 79% purity.

Workup

  1. filtrationfiltered
  2. customThe solvent was removed in vacuo
  3. customto leave a residue which
  4. washwas washed with methanol

Sources & evidence

ORD record
ord-97a2e2f4e88348629c63b492ab1ba7ed
Source dataset
uspto-grants-2010_03
Patent number
US07674906B2

Reaction notes

Loading…