(4-Aminophenoxy)benzene → 4-(4-Phenoxyanilino)benzo[g]quinoline-3-carbonitrile

HRID 2213716Notes

Reaction equation

HRID 2213716 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]3[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=3[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>[O:18]([C:25]1[CH:26]=[CH:27][C:28]([NH:29][C:2]2[C:11]3[C:6](=[CH:7][C:8]4[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=4[CH:10]=3)[N:5]=[CH:4][C:3]=2[C:16]#[N:17])=[CH:30][CH:31]=1)[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

7

Reactant 4

HCID 8764(4-Aminophenoxy)benzeneHCID 10340Sodium CarbonateHCID 98346304-Chlorobenzo[g]quinoline-3-carbonitrileHCID 10176127Pyridinium chloride

Product 1

HCID 102715414-(4-Phenoxyanilino)benzo[g]quinoline-3-carbonitrileYield 73.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8076Glycol monoethyl etherSolvent

Procedure

A reaction mixture of 141.8 mg (0.59 mmol) of 4-chlorobenzo[g]quinoline-3-carbonitrile, 111.1 mg (0.60 mmol) of 4-phenoxyaniline and 57.8 mg (0.50 mmol) of pyridine hydrochloride in 8 ml of 2-ethoxyethanol is heated at 110–120° C. for 1 hour. After cooling, the mixture is diluted with water and made basic by addition of 125.0 mg (1.18 mmol) of sodium carbonate. The precipitate is collected by filtration and washed with water. Drying in vacuo yields the crude product. The crude product is purified by chromatography, eluting with a methylene chloride/methanol gradient from 100:0 to 86:14, to provide 167.8 mg (73.4%) of the pure product as a yellow solid, mp 250–251° C.

Workup

  1. temperatureis heated at 110–120° C. for 1 hour
  2. temperatureAfter cooling
  3. filtrationThe precipitate is collected by filtration
  4. washwashed with water
  5. customDrying in vacuo
  6. customyields the crude product
  7. customThe crude product is purified by chromatography
  8. washeluting with a methylene chloride/methanol gradient from 100:0 to 86:14

Sources & evidence

ORD record
ord-3ba42695cff74d3593139c6a9e960a2d
Source dataset
uspto-grants-2006_09
Patent number
US07105531B2

Reaction notes

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