Sodium Hydroxide → HCID 15621416, compound

HRID 1720261Notes

Reaction equation

HRID 1720261 reaction equation
O[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([N+:12]([O-:14])=[O:13])[CH:10]=2)[N:5]=[C:4]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:3]=1.P(Cl)(Cl)([Cl:23])=O.[OH-].[Na+]>CN(C)C=O>[Cl:23][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([N+:12]([O-:14])=[O:13])[CH:10]=2)[N:5]=[C:4]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:3]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 178526467HCID 178526467, compound

Product 1

HCID 15621416HCID 15621416, compoundYield 102%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

4-Hydroxy-6-nitro-2-phenylquinoline (10.00 g, 38 mmol) was suspended in phosphorus oxychloride (POCl3) (57.58 g, 380 Mol) at 0° C. Dimethylformamide (DMF) (45 ml) was added dropwise and the resulting mixture heated at 70° C. for 5 hours. The reaction was cooled and then poured onto ice. The pH was adjusted to 6 with aqueous sodium hydroxide and the precipitate collected by vacuum filtration and dried in a vacuum oven to give 4-chloro-6-nitro-2-phenylquinoline (10.95 g, 102%) as a yellow powder.

Workup

  1. temperatureThe reaction was cooled
  2. additionpoured onto ice
  3. filtrationthe precipitate collected by vacuum filtration
  4. customdried in a vacuum oven

Sources & evidence

ORD record
ord-c179ae509d47455d9beeffab77671fa2
Source dataset
uspto-grants-1996_04
Patent number
US05506235

Reaction notes

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