3-methyl-6-nitro-1-(2-pyridinyl)-1,9-dihydro-4H-pyrazolo[3,4-b]quinolin-4-one → 6-Amino-3-methyl-1-(2-pyridinyl)-1,9-dihydro-4H-pyrazolo[3,4-b]quinolin-4-one

HRID 498030Notes

Reaction equation

HRID 498030 reaction equation
[CH3:1][C:2]1[C:14]2[C:13](=[O:15])[C:12]3[C:7](=[CH:8][CH:9]=[C:10]([N+:16]([O-])=O)[CH:11]=3)[NH:6][C:5]=2[N:4]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=2)[N:3]=1>CN(C)C=O.[C].[Pd]>[NH2:16][C:10]1[CH:11]=[C:12]2[C:7](=[CH:8][CH:9]=1)[NH:6][C:5]1[N:4]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=3)[N:3]=[C:2]([CH3:1])[C:14]=1[C:13]2=[O:15]

Participants

4

Reactant 1

HCID 1358481013-methyl-6-nitro-1-(2-pyridinyl)-1,9-dihydro-4H-pyrazolo[3,4-b]quinolin-4-one

Product 1

HCID 1358480556-Amino-3-methyl-1-(2-pyridinyl)-1,9-dihydro-4H-pyrazolo[3,4-b]quinolin-4-oneYield 69%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

A solution of 3-methyl-6-nitro-1-(2-pyridinyl)-1,9-dihydro-4H-pyrazolo[3,4-b]quinolin-4-one (4.64 g, 14.4 mmol) and 5% palladium-carbon (4.64 g, 50% hydrate) in N,N-dimethylformamide (400 mL) was stirred at room temperature under hydrogen atmosphere for 4 hours. The reaction solution was filtered to remove the catalyst, and the filtrate was evaporated under reduced pressure. The residue thus obtained was purified by silica gel column chromatography (chloroform:methanol=99:1 to chloroform:methanol=95:5) to give the title compound (2.86 g, 69% yield).

Workup

  1. filtrationThe reaction solution was filtered
  2. customto remove the catalyst
  3. customthe filtrate was evaporated under reduced pressure
  4. customThe residue thus obtained
  5. customwas purified by silica gel column chromatography (chloroform:methanol=99:1 to chloroform:methanol=95:5)

Sources & evidence

ORD record
ord-6d4f74e72db245acbf4d4cdc32d4adca
Source dataset
uspto-grants-2005_09
Patent number
US06949648B2

Reaction notes

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