2,4-Dichloroaniline → 4-[(2,4-Dichlorophenyl)amino]-7-(2-methoxyethoxy)-3-quinolinecarbonitrile

HRID 1837377Notes

Reaction equation

HRID 1837377 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:12][CH2:13][CH2:14][O:15][CH3:16])=[CH:9][CH:10]=2)[N:5]=[CH:4][C:3]=1[C:17]#[N:18].[Cl:19][C:20]1[CH:26]=[C:25]([Cl:27])[CH:24]=[CH:23][C:21]=1[NH2:22].Cl.N1C=CC=CC=1>C(OCCO)C>[Cl:19][C:20]1[CH:26]=[C:25]([Cl:27])[CH:24]=[CH:23][C:21]=1[NH:22][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:12][CH2:13][CH2:14][O:15][CH3:16])=[CH:9][CH:10]=2)[N:5]=[CH:4][C:3]=1[C:17]#[N:18]

Participants

5

Reactant 3

HCID 111232,4-DichloroanilineHCID 10176127Pyridinium chlorideHCID 234980944-Chloro-7-(2-methoxyethoxy)-3-quinolinecarbonitrile

Product 1

HCID 103628074-[(2,4-Dichlorophenyl)amino]-7-(2-methoxyethoxy)-3-quinolinecarbonitrileYield 26.5%

Reagents, catalysts & solvents 1

HCID 8076Glycol monoethyl etherSolvent

Procedure

A mixture of 4-chloro-7-(2-methoxyethoxy)-3-quinolinecarbonitrile (262 mg, 1.0 mmol), 2,4-dichloroaniline (195 mg, 1.2 mmol) and pyridine hydrochloride (140 mg, 1.2 mmol) in 10 mL of 2-ethoxyethanol is heated at reflux for 30 minutes. The reaction mixture is cooled to room temperature partitioned between ethyl acetate and saturated sodium bicarbonate. The organic layer is washed with a 1:1 mixture of saturated sodium bicarbonate and 5 N sodium hydroxide. The organic layer is dried over magnesium sulfate, filtered and concentrated in vacuo. Purification by column chromatography, eluting with a gradient of 1:1 ethyl acetate:hexane to all ethyl acetate provides 103 mg of 4-[(2,4-dichlorophenyl)amino]-7-(2-methoxyethoxy)-3-quinolinecarbonitrile, mp 144-145° C.

Workup

  1. temperatureis heated
  2. temperatureat reflux for 30 minutes
  3. custompartitioned between ethyl acetate and saturated sodium bicarbonate
  4. washThe organic layer is washed with a 1:1 mixture of saturated sodium bicarbonate and 5 N sodium hydroxide
  5. dry with materialThe organic layer is dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customPurification by column chromatography
  9. washeluting with a gradient of 1:1 ethyl acetate

Sources & evidence

ORD record
ord-dde3141e0b4e48cd970d8cb8a4a11121
Source dataset
uspto-grants-2004_08
Patent number
US06780996B2

Reaction notes

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