Sodium Hydroxide → 2-(4-cyano-3-methylphenyl)-3-cyclopentyl-3,3a,4,5-tetrahydro-2H-pyrazolo[3,4-f]quinoline-7-carboxylic acid

HRID 1844841Notes

Reaction equation

HRID 1844841 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH:21]([CH:22]3[CH2:26][CH2:25][CH2:24][CH2:23]3)[CH:20]3[C:11]([C:12]4[CH:13]=[CH:14][C:15]([C:27]([O:29]C)=[O:28])=[N:16][C:17]=4[CH2:18][CH2:19]3)=[N:10]2)=[CH:5][C:4]=1[CH3:31])#[N:2].[OH-].[Na+]>CO.O1CCCC1>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH:21]([CH:22]3[CH2:26][CH2:25][CH2:24][CH2:23]3)[CH:20]3[C:11]([C:12]4[CH:13]=[CH:14][C:15]([C:27]([OH:29])=[O:28])=[N:16][C:17]=4[CH2:18][CH2:19]3)=[N:10]2)=[CH:5][C:4]=1[CH3:31])#[N:2]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 86700924methyl 2-(4-cyano-3-methylphenyl)-3-cyclopentyl-3,3a,4,5-tetrahydro-2H-pyrazolo[3,4-f]quinoline-7-carboxylate

Product 1

HCID 568492242-(4-cyano-3-methylphenyl)-3-cyclopentyl-3,3a,4,5-tetrahydro-2H-pyrazolo[3,4-f]quinoline-7-carboxylic acidYield 36%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

In a dried reaction flask, the crude methyl 2-(4-cyano-3-methylphenyl)-3-cyclopentyl-3,3a,4,5-tetrahydro-2H-pyrazolo[3,4-f]quinoline-7-carboxylate (0.682 g, about 1.5 mmol) and 10% aqueous NaOH solution (1.97 mL, 4.925 mmol) were dissolved in methanol (3 mL) and tetrahydrofuran (8 mL). The reaction solution was stirred at room temperature for 6 hr. The reaction solution was concentrated at a reduced pressure to reduce the volume to half. The residue was adjusted with 1 M HCl under an ice bath to a pH value of 5-6, and filtered to obtain a crude brick red solid, which was then washed with methanol, ethanol and ethyl acetate to produce a solid (0.216 g) in 36.0% yield.

Workup

  1. customIn a dried reaction flask
  2. concentrationThe reaction solution was concentrated at a reduced pressure
  3. filtrationfiltered
  4. customto obtain a crude brick red solid, which
  5. washwas then washed with methanol, ethanol and ethyl acetate

Sources & evidence

ORD record
ord-b729e1d83eaa46e28a13924aa1456f03
Source dataset
uspto-grants-2015_02
Patent number
US08946279B2

Reaction notes

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