Tetrahydrofuran → HCID 135599994, compound

HRID 1175810Notes

Reaction equation

HRID 1175810 reaction equation
[NH2:1][C:2]1[N:3]([C:16]2[CH:17]=[C:18]([CH:23]=[CH:24][CH:25]=2)[C:19](OC)=[O:20])[N:4]=[C:5]2[C:14]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=3[NH:8][C:7](=[O:15])[C:6]=12.[H-].[Al+3].[Li+].[H-].[H-].[H-].O1CCCC1.S([O-])([O-])(=O)=O.[Na+].[Na+]>C(OCC)C>[NH2:1][C:2]1[N:3]([C:16]2[CH:25]=[CH:24][CH:23]=[C:18]([CH2:19][OH:20])[CH:17]=2)[N:4]=[C:5]2[C:14]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=3[NH:8][C:7](=[O:15])[C:6]=12

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 24436Sodium SulfateHCID 21226445Aluminium lithium hydrideHCID 135599895HCID 135599895, compound

Product 1

HCID 135599994HCID 135599994, compoundYield 81.9%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of methyl 3-(3-amino-4-oxo-4,5-dihydro-2H-pyrazolo[4,3-c]quinolin-2-yl)benzoate (80 mg), lithium aluminum hydride (12 mg) and tetrahydrofuran (5 ml) was stirred at room temperature for 3 hours. Diethyl ether and then saturated aqueous sodium sulfate solution were added to the reaction mixture, and the organic layer was separated by decantation. The organic layer was dried over anhydrous magnesium sulfate and the solvent was distilled off under reduced pressure. Diisopropy ether was added to the residue. The precipitated solid was collected by filtration, washed with diisopropyl ether, and dried to obtain the target compound (60 mg).

Workup

  1. customthe organic layer was separated by decantation
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. distillationthe solvent was distilled off under reduced pressure
  4. additionDiisopropy ether was added to the residue
  5. filtrationThe precipitated solid was collected by filtration
  6. washwashed with diisopropyl ether
  7. customdried

Sources & evidence

ORD record
ord-88e2e91353d44418b344041e281180c8
Source dataset
uspto-grants-2010_11
Patent number
US07842701B2

Reaction notes

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