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Hydrochloric Acid → 1-ethyl-3-methyl-N-(phenylmethyl)-1H-pyrazolo[3,4-b]quinolin-4-amine

HRID 1456027
Notes
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Reaction equation

HRID 1456027 reaction equation
[CH2:1]([N:3]1[C:7]2=[N:8][C:9]3[C:14]([C:15](Cl)=[C:6]2[C:5]([CH3:17])=[N:4]1)=[CH:13][CH:12]=[CH:11][CH:10]=3)[CH3:2].[CH2:18]([NH2:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[NH4+].[OH-].Cl>C(Cl)Cl.O.CS(C)=O>[CH2:1]([N:3]1[C:7]2=[N:8][C:9]3[C:14]([C:15]([NH:25][CH2:18][C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)=[C:6]2[C:5]([CH3:17])=[N:4]1)=[CH:13][CH:12]=[CH:11][CH:10]=3)[CH3:2]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 7504BenzylamineHCID 14923Ammonium HydroxideHCID 195922341-ethyl-3-methyl-4-chloro-1H-pyrazolo[3,4-b]quinoline

Product 1

HCID 700874621-ethyl-3-methyl-N-(phenylmethyl)-1H-pyrazolo[3,4-b]quinolin-4-amineYield 66.2%

Reagents, catalysts & solvents 3

HCID 679
Dimethyl Sulfoxide
Solvent
HCID 962WaterSolvent
HCID 6344DichloromethaneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 1-ethyl-3-methyl-4-chloro-1H-pyrazolo[3,4-b]quinoline (1.0 g, 4.3 mmol), DMSO (3 ml) and benzylamine (0.98 ml, 9 mmol) was heated at 80° C. overnight. The reaction mixture was poured into water (100 ml), then NH4OH (0.5 ml) was added. The mixture was extracted with CH2Cl2 (200 ml) and the CH2Cl2 was concentrated to about 20 ml and then this solution was purified by column chromatography on silica gel, followed by high pressure liquid chromatography eluting with 20% ethyl acetate/hexane to afford the product as the free base. The free base was dissolved in CH2Cl2 (20 ml) and treated with ethereal HCl. The mixture was evaporated and the residue was crystallized from ether to afford 0.9 g of 1-ethyl-3-methyl-N-(phenylmethyl)-1H-pyrazolo[3,4-b]quinolin-4amine.HCl, as an off white solid, m.p. 228°-231° C.

Workup

  1. extractionThe mixture was extracted with CH2Cl2 (200 ml)
  2. concentrationthe CH2Cl2 was concentrated to about 20 ml
  3. customthis solution was purified by column chromatography on silica gel
  4. washeluting with 20% ethyl acetate/hexane
  5. customto afford the product as the free base
  6. customThe mixture was evaporated
  7. customthe residue was crystallized from ether

Sources & evidence

ORD record
ord-d0130e50782548ba88229eb878adb914
Source dataset
uspto-grants-1998_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05843956

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes