Methanol → HCID 56849102, compound

HRID 1844838Notes

Reaction equation

HRID 1844838 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:10]2[CH:22]([CH:23]3[CH2:27][CH2:26][CH2:25][CH2:24]3)[CH:21]3[C:12]([C:13]4[CH:14]=[CH:15][C:16]([C:28]([O:30]C)=[O:29])=[N:17][C:18]=4[CH2:19][CH2:20]3)=[N:11]2)[CH:5]=[CH:6][C:7]=1[C:8]#[N:9].[OH-].[Na+].CO>O1CCCC1>[Cl:1][C:2]1[CH:3]=[C:4]([N:10]2[CH:22]([CH:23]3[CH2:27][CH2:26][CH2:25][CH2:24]3)[CH:21]3[C:12]([C:13]4[CH:14]=[CH:15][C:16]([C:28]([OH:30])=[O:29])=[N:17][C:18]=4[CH2:19][CH2:20]3)=[N:11]2)[CH:5]=[CH:6][C:7]=1[C:8]#[N:9]

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 68010258HCID 68010258, compound

Product 1

HCID 56849102HCID 56849102, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a dried reaction flask, methyl 2-(3-chloro-4-cyanophenyl)-3-cyclopentyl-3,3a,4,5-tetrahydro-2H-pyrazolo[3,4-f]quinoline-7-carboxylate (0.868 g, 2.0 mmol) and 10% aqueous NaOH solution (2.4 mL, 6.0 mmol) were dissolved into a mixture of methanol (4 mL) and tetrahydrofuran (10 mL). The reaction solution was stirred at room temperature for 15 hr. The solution was concentrated at a reduced pressure to reduce half of the volume. The residue was adjusted with 1 M HCl under an ice bath to a pH value of 2-3, and filtered to obtain a crude yellow solid, which was then washed with ethanol and ethyl ether to obtain a solid (0.496 g) in 59.0% yield.

Workup

  1. concentrationThe solution was concentrated at a reduced pressure
  2. filtrationfiltered
  3. customto obtain a crude yellow solid, which
  4. washwas then washed with ethanol and ethyl ether

Sources & evidence

ORD record
ord-7181d20d58974ecb9f1bd3c539d2752b
Source dataset
uspto-grants-2015_02
Patent number
US08946279B2

Reaction notes

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