Dimethylformamide → HCID 15021555, compound

HRID 465383Notes

Reaction equation

HRID 465383 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1F)[N:8]([CH2:13][CH3:14])[CH:7]=[C:6]([C:15]([OH:17])=[O:16])[C:5]2=[O:18].[CH3:19][N:20]1[CH2:25][CH2:24][CH:23]([OH:26])[CH2:22][CH2:21]1.CN(C=O)C.[H-].[Na+]>O.C(Cl)(Cl)Cl.C(O)(=O)C>[CH3:19][N:20]1[CH2:25][CH2:24][CH:23]([O:26][C:11]2[CH:10]=[C:9]3[C:4]([C:5](=[O:18])[C:6]([C:15]([OH:17])=[O:16])=[CH:7][N:8]3[CH2:13][CH3:14])=[CH:3][C:2]=2[F:1])[CH2:22][CH2:21]1

Participants

8

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 660484-Piperidinol, 1-methyl-HCID 8005211-Ethyl-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

Product 1

HCID 15021555HCID 15021555, compoundYield 9.9%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

To a mixture of 280 mg of 6,7-difluoro-1-ethyl-1,4-dihydro-4-oxoquinoline-3-carboxylic acid, 345 mg of N-methyl-4-piperidinol and 4 ml of DMF was added 200 mg of 50% sodium hydride while the former was stirred under ice cooling. After the resultant mixture was stirred for 2 hours at room temperature, 260 mg of acetic acid was added, followed by the addition of chloroform and water. The resultant mixture was thoroughly shaken and mixed. The chloroform layer was collected, washed with water, and then dried over sodium sulfate. The solvent was distilled off under reduced pressure. A solid thus precipitated was collected by filtration, whereby 38 mg of the title compound was obtained.

Workup

  1. additionmixed
  2. customThe chloroform layer was collected
  3. washwashed with water
  4. dry with materialdried over sodium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. customA solid thus precipitated
  7. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-52a2e0543ae546c3b134df7045c421ff
Source dataset
uspto-grants-1992_10
Patent number
US05153203

Reaction notes

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