Phosphorus oxychloride → 4-Chloro-1-methyl-2-oxo-1,2-dihydroquinoline-3-carbonitrile

HRID 970466Notes

Reaction equation

HRID 970466 reaction equation
C1([NH:7][C:8]([C:10]2[C:11](=[O:22])[N:12]([CH3:21])[C:13]3[C:18]([C:19]=2O)=[CH:17][CH:16]=[CH:15][CH:14]=3)=O)CCCCC1.P(Cl)(Cl)([Cl:25])=O>>[Cl:25][C:19]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[N:12]([CH3:21])[C:11](=[O:22])[C:10]=1[C:8]#[N:7]

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 54685659N-cyclohexyl-4-hydroxy-1-methyl-2-oxo-1,2-dihydroquinoline-3-carboxamide

Product 1

HCID 27857484-Chloro-1-methyl-2-oxo-1,2-dihydroquinoline-3-carbonitrileYield 82%

Procedure

A solution of Compound 2 (1.5 g, 5 mmol) in 20 mL 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 903 mg (82%) of white solids. M.P. 235° C. 1H NMR (DMSO-d6): 3.66 (s, 3H), 7.50 (t, J=7.7 Hz, 1H), 7.74 (d, J=8.6 Hz, 1H), 7.91 (t, J=8.7 Hz, 1H), 8.08 (d, J=7.6 Hz, 1H). EIMS m/z 219 (M+1), 241 (M+23). Anal. (C17H7ClN2O) 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-05b8263375ed496394ed1e76d9b5d4c1
Source dataset
uspto-grants-2007_12
Patent number
US07312220B2

Reaction notes

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