Phosphorus oxychloride → HCID 66820545, compound

HRID 241011Notes

Reaction equation

HRID 241011 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]2[C:14](=O)[CH:13]=[CH:12][NH:11][C:10]=2[CH3:16])[CH:5]=[CH:6][CH:7]=1.P(Cl)(Cl)([Cl:19])=O>>[Cl:19][C:14]1[CH:13]=[CH:12][N:11]=[C:10]([CH3:16])[C:9]=1[CH2:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[CH:3]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 66820160HCID 66820160, compound

Product 1

HCID 66820545HCID 66820545, compound

Procedure

A solution of 3-[(3-fluorophenyl)methyl)-2-methylpyridin-4(1H)-one (0.07 g, 0.32 mmol) in phosphorous oxychloride (3 mL) was heated to 55° C. for 16 h. Then the solution was cooled to room temperature and concentrated. The remaining residue was dissolved in ethyl acetate (10 mL), washed with 5% sodium bicarbonate (2×5 mL), and saturated sodium chloride (5 mL), dried over sodium sulfate, filtered and concentrated to afford 4-chloro-3-[(3-fluorophenyl)methyl]-2-methylpyridine. 1H NMR (400 MHz, CDCl3): 8.33 (d. 1H), 7.30-7.23 (m, 2H), 6.92-6.85 (m, 2H), 6.76 (d, 1H), 4.22 (s, 2H), 2.54 (s, 3H). MS (EI) for C13H11ClF: 236.0 (MH+).

Workup

  1. concentrationconcentrated
  2. dissolutionThe remaining residue was dissolved in ethyl acetate (10 mL)
  3. washwashed with 5% sodium bicarbonate (2×5 mL), and saturated sodium chloride (5 mL)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-bec4e8468054493b92417ce6a222fdfa
Source dataset
uspto-grants-2014_02
Patent number
US08648066B2

Reaction notes

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