Quinoline → 2,3-Dichloro-5-nitropyridine

HRID 1993633Notes

Reaction equation

HRID 1993633 reaction equation
P(Cl)(Cl)([Cl:3])=O.N1C2C(=CC=CC=2)C=CC=1.[Cl:16][C:17]1[C:18](O)=[N:19][CH:20]=[C:21]([N+:23]([O-:25])=[O:24])[CH:22]=1>>[Cl:3][C:18]1[C:17]([Cl:16])=[CH:22][C:21]([N+:23]([O-:25])=[O:24])=[CH:20][N:19]=1

Participants

4

Reactant 3

HCID 7047QuinolineHCID 24813Phosphorus oxychlorideHCID 178526838HCID 178526838, compound

Product 1

HCID 27631062,3-Dichloro-5-nitropyridineYield 86%

Procedure

Place phosphorus oxychloride (11.28 mL, 121 mmol) in a round-bottom flask and cool to 0° C. Add quinoline (7.15 mL, 60.5 mmol) followed by 3-chloro-5-nitro-pyridin-2-ol (21.13 g, 121 mmol) in portions. Heat reaction to 120° C. for 2 hours. Pour reaction onto ice and triturate with water. Filter off the solid and wash with water. Dry thoroughly to yield 19.95 g (86%) of the title compound: 1H NMR δH (400 MHz, DMSO) 9.20 (s, 1H), 8.97 (s, 1H).

Workup

  1. temperatureHeat
  2. customreaction to 120° C. for 2 hours
  3. additionPour
  4. customreaction onto ice
  5. customtriturate with water
  6. filtrationFilter off the solid
  7. washwash with water
  8. customDry thoroughly

Sources & evidence

ORD record
ord-d04a93bd4cfb44b2a4366abbc52229da
Source dataset
uspto-grants-2010_01
Patent number
US07652015B2

Reaction notes

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