Carbon Dioxide → HCID 67203453, compound

HRID 548598Notes

Reaction equation

HRID 548598 reaction equation
[CH2:1]([N:4]1[CH:16]=[C:15]2[C:6]([C:7](=[O:17])[NH:8][C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][C:14]=32)=[N:5]1)[CH2:2][CH3:3].CN(C)CCN(C)C.C([Li])CCC.[C:31](=[O:33])=[O:32]>CCCCCC.O.C(OCC)C.O1CCCC1>[O:17]=[C:7]1[C:6]2=[N:5][N:4]([CH2:1][CH2:2][CH3:3])[C:16]([C:31]([OH:33])=[O:32])=[C:15]2[C:14]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[NH:8]1

Participants

9

Reactant 4

HCID 280Carbon DioxideHCID 8037N,N,N',N'-TetramethylethylenediamineHCID 67203277HCID 67203277, compoundHCID 178418339Butyllithium

Product 1

HCID 67203453HCID 67203453, compoundYield 56.3%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Conditions

Temperature
5 °C

Procedure

A 12 L reaction vessel was charged with 2-propyl-2,5-dihydro-4H-pyrazolo[3,4-c]quinolin-4-one (103.40 g, 455 mmol), tetrahydrofuran (THF, 6.1 L), and N,N,N′,N′-tetramethylethylenediamine (392 mL, 2.59 mol), and the resulting suspension was cooled in an ice bath. n-Butyllithium (510 mL of a 2.5 M solution in hexane, 1.27 mol) was added over 65 minutes, and the reaction was allowed to stir at 5° C. for 20 minutes. The contents of the 12 L vessel were transferred via cannula over a period of 20 minutes to a 22 L vessel containing dry ice (3 kg) and diethyl ether (2 L). The reaction was stirred overnight, water (3 L) was added, the organic layer was drawn off, and the aqueous layer was washed with chloroform (4×500 mL). The aqueous layer was acidified by treatment with 2 M HCl (1.6 L), and the resulting suspension was stirred overnight. The solid was collected by filtration and dried on suction for 2 days to afford 69.47 g of 4-oxo-2-propyl-4,5-dihydro-2H-pyrazolo[3,4-c]quinoline-1-carboxylic acid as an off-white solid.

Workup

  1. customA 12 L reaction vessel
  2. temperaturethe resulting suspension was cooled in an ice bath
  3. waitThe contents of the 12 L vessel were transferred via cannula over a period of 20 minutes to a 22 L vessel
  4. stirringThe reaction was stirred overnight
  5. washthe aqueous layer was washed with chloroform (4×500 mL)
  6. stirringthe resulting suspension was stirred overnight
  7. filtrationThe solid was collected by filtration
  8. customdried on suction for 2 days

Sources & evidence

ORD record
ord-605b8eee2f914bc690797786203ddc86
Source dataset
uspto-grants-2011_05
Patent number
US07943610B2

Reaction notes

Loading…