Toluene → 4-(3-Chloro-4-fluoroanilino)-7-(4-methyl-1-piperazinyl)-6-nitro-3-quinolinecarbonitrile

HRID 548501Notes

Reaction equation

HRID 548501 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:22]=[CH:23][C:24]=1[F:25])[NH:5][C:6]1[C:15]2[C:10](=[CH:11][C:12](Cl)=[C:13]([N+:16]([O-:18])=[O:17])[CH:14]=2)[N:9]=[CH:8][C:7]=1[C:20]#[N:21].[CH3:26][N:27]1[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]1.C1(C)C=CC=CC=1>CC(C)=O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:22]=[CH:23][C:24]=1[F:25])[NH:5][C:6]1[C:15]2[C:10](=[CH:11][C:12]([N:30]3[CH2:31][CH2:32][N:27]([CH3:26])[CH2:28][CH2:29]3)=[C:13]([N+:16]([O-:18])=[O:17])[CH:14]=2)[N:9]=[CH:8][C:7]=1[C:20]#[N:21]

Participants

5

Reactant 3

HCID 1140TolueneHCID 531671-MethylpiperazineHCID 216973054-(3-Chloro-4-fluoroanilino)-7-chloro-6-nitro-3-quinolinecarbonitrile

Product 1

HCID 216973254-(3-Chloro-4-fluoroanilino)-7-(4-methyl-1-piperazinyl)-6-nitro-3-quinolinecarbonitrile

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A stirred mixture of 4-(3-chloro-4-fluoroanilino)-7-chloro-6-nitro-3-quinolinecarbonitrile (1.88 g, 5.0 mmol), N-methylpiperazine (5 ml, 45 mmol), and 10 ml of toluene was refluxed for 45 m, evaporated to remove volatile matter, and stirred in water with potassium carbonate (2.75 g). The resulting solid was filtered, washed with water, and dried to give 2.26 g. An acetone solution was passed onto a pad of silica gel; elution with 50:2:1 acetone-MeOH-TEA and evaporation gave a red solid, mp 240-246°; ms 441.2 (M+H)+, 221.2 (M+2H)+2.

Workup

  1. temperaturewas refluxed for 45 m
  2. customevaporated
  3. customto remove volatile matter
  4. filtrationThe resulting solid was filtered
  5. washwashed with water
  6. customdried
  7. customto give 2.26 g
  8. washelution
  9. customwith 50:2:1 acetone-MeOH-TEA and evaporation
  10. customgave a red solid, mp 240-246°

Sources & evidence

ORD record
ord-d4b9e10e8cf04903830911eacaee9931
Source dataset
uspto-grants-2011_05
Patent number
USRE042376E1

Reaction notes

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