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

HRID 977121Notes

Reaction equation

HRID 977121 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) was heated at 80° C. overnight. The reaction mixture was poured into ice/water and the gummy solid which formed was collected by filtration. The solid was dissolved in ethyl acetate, dried over MgSO4, filtered and concentrated. The residual oil was 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. filtrationwas collected by filtration
  3. dissolutionThe solid was dissolved in ethyl acetate
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residual oil was crystallized from ethyl acetate

Sources & evidence

ORD record
ord-387c04f5cfb0450782cbd8b5f1364a67
Source dataset
uspto-grants-1997_03
Patent number
US05614530

Reaction notes

Loading…