Benzylamine → 1-ethyl-N-(phenyl methyl)-1H-pyrazolo[3,4-b]quinolin-4-amine

HRID 1458729Notes

Reaction equation

HRID 1458729 reaction equation
[CH2:1]([N:3]1[C:7]2=[N:8][C:9]3[C:14]([C:15](Cl)=[C:6]2[CH:5]=[N:4]1)=[CH:13][CH:12]=[CH:11][CH:10]=3)[CH3:2].[CH2:17]([NH2:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CS(C)=O>[CH2:1]([N:3]1[C:7]2=[N:8][C:9]3[C:14]([C:15]([NH:24][CH2:17][C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)=[C:6]2[CH:5]=[N:4]1)=[CH:13][CH:12]=[CH:11][CH:10]=3)[CH3:2]

Participants

4

Reactant 2

HCID 7504BenzylamineHCID 158169081-ethyl-4-chloro-1H-pyrazolo[3,4-b]quinoline

Product 1

HCID 98178721-ethyl-N-(phenyl methyl)-1H-pyrazolo[3,4-b]quinolin-4-amineYield 92%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 1-ethyl-4-chloro-1H-pyrazolo[3,4-b]quinoline (15.0 g, 0.065 mol), benzylamine (15.6 ml, 0.14 mol) and DMSO (100 ml) is heated at 80° C. overnight. The reaction mixture is poured into ice/water and the gummy solid which formed is collected by filtration. The solid is dissolved in ethyl acetate, dried over MgSO4, filtered and concentrated. The residual oil is crystallized from ethyl acetate to afford 18 g (92%) of 1-ethyl-N-(phenyl methyl)-1H-pyrazolo[3,4-b]quinolin-4-amine, m.p. 130°-132° C.

Workup

  1. customthe gummy solid which formed
  2. filtrationis collected by filtration
  3. dissolutionThe solid is dissolved in ethyl acetate
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residual oil is crystallized from ethyl acetate

Sources & evidence

ORD record
ord-f3667fa46f094b3e9535b916ddcd129b
Source dataset
uspto-grants-1998_12
Patent number
US05852035

Reaction notes

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