Phosphorus oxychloride → 4-Chloro-1-(4-fluorobenzyl)-2-oxo-1,2-dihydro-quinoline-3-carbonitrile

HRID 970471Notes

Reaction equation

HRID 970471 reaction equation
C1([NH:7][C:8]([C:10]2[C:11](=[O:29])[N:12]([CH2:21][C:22]3[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=3)[C:13]3[C:18]([C:19]=2O)=[CH:17][CH:16]=[CH:15][CH:14]=3)=O)CCCCC1.P(Cl)(Cl)([Cl:32])=O>>[Cl:32][C:19]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[N:12]([CH2:21][C:22]2[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=2)[C:11](=[O:29])[C:10]=1[C:8]#[N:7]

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 587991691-(4-Fluorobenzyl)-4-hydroxy-2-oxo-1,2-dihydro-quinoline-3-carboxylic acid cyclohexylamide

Product 1

HCID 210819574-Chloro-1-(4-fluorobenzyl)-2-oxo-1,2-dihydro-quinoline-3-carbonitrileYield 76%

Procedure

A solution of Compound 7 (0.7 g, 1.77 mmol) in 20 mL neat phosphorus oxychloride was heated at 90° C. for 2 h. The solvent was evaporated under reduced pressure. The residue was suspended in ice water and neutralized by solid sodium bicarbonate. The solids formed were filtered, washed by water, and purified by flash chromatography eluting with 1% methanol in dichloromethane to yield 420 mg (76%) of white solids. M.P. 231° C. 1H NMR (DMSO-d6): δ 5.54 (s, 2H), 7.13 (m, 2H), 7.34 (m, 2H), 7.46 (t, J=7.5 Hz, 1H), 7.55 (d, J=8.5 Hz, 1H), 7.80 (t, J=8.4 Hz, 1H), 8.12 (d, J=7.9 Hz, 1H). EIMS m/z 335 (M+23). Anal. (C17H10ClFN2O) C, H, N.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. customThe solids formed
  3. filtrationwere filtered
  4. washwashed by water
  5. custompurified by flash chromatography
  6. washeluting with 1% methanol in dichloromethane

Sources & evidence

ORD record
ord-8ce4276622be44be822c1e4707201ae6
Source dataset
uspto-grants-2007_12
Patent number
US07312220B2

Reaction notes

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