Sodium Hydroxide → 7-methyl-4-oxo-1-(tetrahydro-2H-pyran-4-yl)-4,5-dihydro-1H-pyrazolo[4,3-c]quinoline-8-carboxylic acid

HRID 69108

Reaction equation

HRID 69108 reaction equation
[CH3:1][C:2]1[C:3]([C:22]([O:24]C)=[O:23])=[CH:4][C:5]2[C:6]3[N:15]([CH:16]4[CH2:21][CH2:20][O:19][CH2:18][CH2:17]4)[N:14]=[CH:13][C:7]=3[C:8](=[O:12])[NH:9][C:10]=2[CH:11]=1.[OH-].[Na+]>CO>[CH3:1][C:2]1[C:3]([C:22]([OH:24])=[O:23])=[CH:4][C:5]2[C:6]3[N:15]([CH:16]4[CH2:17][CH2:18][O:19][CH2:20][CH2:21]4)[N:14]=[CH:13][C:7]=3[C:8](=[O:12])[NH:9][C:10]=2[CH:11]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 136336855methyl 7-methyl-4-oxo-1-(tetrahydro-2H-pyran-4-yl)-4,5-dihydro-1H-pyrazolo[4,3-c]quinoline-8-carboxylate

Product 1

HCID 1363368547-methyl-4-oxo-1-(tetrahydro-2H-pyran-4-yl)-4,5-dihydro-1H-pyrazolo[4,3-c]quinoline-8-carboxylic acidYield 98.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

To a mixture of 2.63 g of methyl 7-methyl-4-oxo-1-(tetrahydro-2H-pyran-4-yl)-4,5-dihydro-1H-pyrazolo[4,3-c]quinoline-8-carboxylate and 52 mL of methanol was added 10.2 mL of a 3 M aqueous sodium hydroxide solution, followed by stirring at 60° C. for 20 hours. The insoluble material was filtered, and the filtrate was adjusted to pH 2 with concentrated hydrochloric acid, and stirred for 1 hour. The precipitated powder was collected by filtration and dried under reduced pressure to obtain 2.49 g of 7-methyl-4-oxo-1-(tetrahydro-2H-pyran-4-yl)-4,5-dihydro-1H-pyrazolo[4,3-c]quinoline-8-carboxylic acid as powder.

Workup

  1. filtrationThe insoluble material was filtered
  2. stirringstirred for 1 hour
  3. filtrationThe precipitated powder was collected by filtration
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-ba43329c408d4d9782bb8724991c6992
Source dataset
uspto-grants-2014_09
Patent number
US08822448B2

Linked notes

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