Phosphorus oxychloride → 4-Chloro-3-nitro-7-phenylquinoline

HRID 9362Notes

Reaction equation

HRID 9362 reaction equation
P(Cl)(Cl)([Cl:3])=O.[N+:6]([C:9]1[CH:10]=[N:11][C:12]2[C:17]([C:18]=1O)=[CH:16][CH:15]=[C:14]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH:13]=2)([O-:8])=[O:7]>CN(C)C=O>[Cl:3][C:18]1[C:17]2[C:12](=[CH:13][C:14]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[CH:15][CH:16]=2)[N:11]=[CH:10][C:9]=1[N+:6]([O-:8])=[O:7]

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178418967HCID 178418967, compound

Product 1

HCID 219843354-Chloro-3-nitro-7-phenylquinoline

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of phosphorous oxychloride (3.1 g, 20 mmol) in anhydrous N,N-dimethylformamide (DMF, 14 mL) was added to a suspension of 3-nitro-7-phenylquinolin-4-ol (5.0 g, 18.8 mmol) in 80 mL of DMF over 3 min. The reaction was allowed to stir for 1.5 h and then poured into 250 mL crushed ice. The resulting precipitate was collected by filtration, washed with H2O, and dried under vacuum for 2 h. The crude 4-chloro-3-nitro-7-phenylquinoline thus obtained was used without further purification.

Workup

  1. additionpoured into 250 mL
  2. customcrushed ice
  3. filtrationThe resulting precipitate was collected by filtration
  4. washwashed with H2O
  5. customdried under vacuum for 2 h

Sources & evidence

ORD record
ord-ba70021346be4b7b8d28ff373488a299
Source dataset
uspto-grants-2006_08
Patent number
US07091214B2

Reaction notes

Loading…