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

HRID 1818112Notes

Reaction equation

HRID 1818112 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-10ac348a42d848aa97598a5345faf9b4
Source dataset
uspto-grants-2009_10
Patent number
US07598382B2

Reaction notes

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