(4-Aminophenoxy)benzene → 7-Chloro-6-nitro-4-(4-phenoxyanilino)-3-quinolinecarbonitrile

HRID 989307Notes

Reaction equation

HRID 989307 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([Cl:15])=[C:9]([N+:12]([O-:14])=[O:13])[CH:10]=2)[N:5]=[CH:4][C:3]=1[C:16]#[N:17].[O:18]([C:25]1[CH:31]=[CH:30][C:28]([NH2:29])=[CH:27][CH:26]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.Cl.N1C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>C(OCCO)C.O>[Cl:15][C:8]1[CH:7]=[C:6]2[C:11]([C:2]([NH:29][C:28]3[CH:27]=[CH:26][C:25]([O:18][C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)=[CH:31][CH:30]=3)=[C:3]([C:16]#[N:17])[CH:4]=[N:5]2)=[CH:10][C:9]=1[N+:12]([O-:14])=[O:13]

Participants

7

Reactant 4

HCID 8764(4-Aminophenoxy)benzeneHCID 10340Sodium CarbonateHCID 10176127Pyridinium chlorideHCID 219564524,7-Dichloro-6-nitroquinoline-3-carbonitrile

Product 1

HCID 219564207-Chloro-6-nitro-4-(4-phenoxyanilino)-3-quinolinecarbonitrileYield 73.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8076Glycol monoethyl etherSolvent

Conditions

Temperature
115 °C

Procedure

A mixture of 722.7 mg (2.70 mmol) of 4,7-dichloro-6-nitro-3-quinolinecarbonitrile, 100.1 mg (2.70 mmol) of 4-phenoxyaniline and 312.1 mg (2.70 mmol) of pyridine hydrochloride in 30 mL of 2-ethoxyethanol is heated at 110-120° C. for 3 hours. After cooling, the mixture is diluted with water, neutralized with an aqueous solution of saturated sodium carbonate, and extracted with ethyl acetate. The separated organic layer is washed with brine and dried over sodium sulfate. Removal of the solvent yields a solid residue which is purified by flash chromatography (elution with 99:1 methylene chloride/methanol), giving 831.0 mg (73.9%) of the product as a deep yellow solid, mp 220-222° C.

Workup

  1. temperatureAfter cooling
  2. extractionextracted with ethyl acetate
  3. washThe separated organic layer is washed with brine
  4. dry with materialdried over sodium sulfate
  5. customRemoval of the solvent
  6. customyields a solid residue which
  7. customis purified by flash chromatography (elution with 99:1 methylene chloride/methanol)

Sources & evidence

ORD record
ord-e08c241bfef84d4da7a93e55627a6344
Source dataset
uspto-grants-2003_10
Patent number
US06638929B2

Reaction notes

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