Phosphorus oxychloride → HCID 86612776, compound

HRID 2364214Notes

Reaction equation

HRID 2364214 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]2[CH:11]=[C:12]([N+:17]([O-:19])=[O:18])[C:13](O)=[N:14][CH:15]=2)[CH:5]=[CH:6][C:7]=1[F:8].P(Cl)(Cl)([Cl:22])=O>>[Cl:22][C:13]1[C:12]([N+:17]([O-:19])=[O:18])=[CH:11][C:10]([CH2:9][C:4]2[CH:5]=[CH:6][C:7]([F:8])=[C:2]([F:1])[CH:3]=2)=[CH:15][N:14]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178526519HCID 178526519, compound

Product 1

HCID 86612776HCID 86612776, compound

Conditions

Temperature
110 °C

Procedure

A mixture of 5-[(3,4-difluorophenyl)methyl]-3-nitro-2-pyridinol (10.49 g, 39.40 mmol) and phosphorous oxychloride (18 ml) was heated at 110° C. for 4 h and allowed to stir at room temperature overnight. The reaction was quenched by diluting with EtOAc and carefully adding water. The organic layer was washed three times with a saturated solution of NaHCO3 in water, dried and concentrated in vacuo to afford the product as an amber oil. 1H NMR (CDCl3) δ 8.46 (1H, s), 7.95 (1H, s), 7.19-7.14 (1H, m), 7.00-6.96 (1H, m), 6.91-6.88 (1H, m), 4.03 (2H, s).

Workup

  1. customThe reaction was quenched
  2. additionby diluting with EtOAc and carefully adding water
  3. washThe organic layer was washed three times with a saturated solution of NaHCO3 in water
  4. customdried
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0c0b9936fa55473bbfe420b82ca93e1d
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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