Water → HCID 68445078, compound

HRID 502940Notes

Reaction equation

HRID 502940 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:15](=[O:16])[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([C:17](=[O:19])[CH3:18])[CH:13]=2)[NH:8][CH:7]=1)=[O:5])[CH3:2].[F:20][C:21]1[CH:26]=[CH:25][C:24]([CH2:27]Cl)=[CH:23][CH:22]=1.C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C>[CH2:1]([O:3][C:4]([C:6]1[C:15](=[O:16])[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([C:17](=[O:19])[CH3:18])[CH:13]=2)[N:8]([CH2:27][C:24]2[CH:25]=[CH:26][C:21]([F:20])=[CH:22][CH:23]=2)[CH:7]=1)=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 96024-Fluorobenzyl chlorideHCID 11430Potassium CarbonateHCID 735356Ethyl 6-acetyl-1,4-dihydro-4-oxo-3-quinolinecarboxylate

Product 1

HCID 68445078HCID 68445078, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A suspension of ester compound 8 (0.6 g, 2.3 mmol) 4-fluorophenylmethyl chloride (0.97 g, 6.8 mmol) and anhydrous K2CO3 (0.44 g, 6.8 mmol) in dry DMF (20 mL) was stirred for 18 hours at 100° C. After this time the mixture was poured into water (100 mL) and the solid that precipitated was filtered, washed with water, ethanol and light petroleum ether, in turn, and finally dried under IR lamp to give compound 9 (0.75 g, 95%); mp 207-209° C. (washed with dry ethanol).

Workup

  1. customthe solid that precipitated
  2. filtrationwas filtered
  3. washwashed with water, ethanol and light petroleum ether, in turn
  4. customfinally dried under IR lamp

Sources & evidence

ORD record
ord-06b45bcfc21d4fafa01e42a39ab9e49c
Source dataset
uspto-grants-2010_08
Patent number
US07776883B2

Reaction notes

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