Quinoline → 2,3-Dichloro-5-nitropyridine

HRID 1661039Notes

Reaction equation

HRID 1661039 reaction equation
N1C2C(=CC=CC=2)C=CC=1.O=P(Cl)(Cl)[Cl:13].O[C:17]1[C:22]([Cl:23])=[CH:21][C:20]([N+:24]([O-:26])=[O:25])=[CH:19][N:18]=1>>[Cl:13][C:17]1[C:22]([Cl:23])=[CH:21][C:20]([N+:24]([O-:26])=[O:25])=[CH:19][N:18]=1

Participants

4

Reactant 3

HCID 7047QuinolineHCID 24813Phosphorus oxychlorideHCID 178526838HCID 178526838, compound

Product 1

HCID 27631062,3-Dichloro-5-nitropyridine

Conditions

Temperature
120 °C

Procedure

Quinoline (0.3 mL, 2.34 mmol) was added to POCl3 (0.5 mL 4.68 mmol) at 0° C. under nitrogen. To this stirred mixture was added 2-hydroxy-3-chloro-5-nitro pyridine (816 mg, 4.68 mmol) obtained in step i above. The reaction mixture was heated at 120° C. for 2 hours, cooled to 0° C. followed by addition of ice-cold water. The precipitate obtained was filtered, washed thoroughly with water and dried to obtain 2,3-dichloro-5-nitro pyridine.

Workup

  1. temperaturecooled to 0° C.
  2. additionfollowed by addition of ice-cold water
  3. customThe precipitate obtained
  4. filtrationwas filtered
  5. washwashed thoroughly with water
  6. customdried

Sources & evidence

ORD record
ord-9cc45c85bca041a5af9b667c88440071
Source dataset
uspto-grants-2011_10
Patent number
US08030324B2

Reaction notes

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