4-Benzyloxy-3-chloroaniline → N-{4-[4-(Benzyloxy)-3-chloroanilino]-3-cyano-7-ethoxy-6-quinolinyl}acetamide

HRID 748620Notes

Reaction equation

HRID 748620 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:16][CH2:17][CH3:18])=[C:9]([NH:12][C:13](=[O:15])[CH3:14])[CH:10]=2)[N:5]=[CH:4][C:3]=1[C:19]#[N:20].[CH2:21]([O:28][C:29]1[CH:34]=[CH:33][C:32]([NH2:35])=[CH:31][C:30]=1[Cl:36])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.Cl.N1C=CC=CC=1>C(O)(C)C>[CH2:21]([O:28][C:29]1[CH:34]=[CH:33][C:32]([NH:35][C:2]2[C:11]3[C:6](=[CH:7][C:8]([O:16][CH2:17][CH3:18])=[C:9]([NH:12][C:13](=[O:15])[CH3:14])[CH:10]=3)[N:5]=[CH:4][C:3]=2[C:19]#[N:20])=[CH:31][C:30]=1[Cl:36])[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

5

Reactant 3

HCID 12682854-Benzyloxy-3-chloroanilineHCID 10176127Pyridinium chlorideHCID 11358234N-(4-Chloro-3-cyano-7-ethoxy-6-quinolinyl)acetamide

Product 1

HCID 67315262N-{4-[4-(Benzyloxy)-3-chloroanilino]-3-cyano-7-ethoxy-6-quinolinyl}acetamide

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of 4.17 g (0.0149 moles) of the N-(4-chloro-3-cyano-7-ethoxy-6-quinolinyl)acetamide, 4.04 g (0.0173 moles) of 4-benzyloxy-3-chloro-phenylamine (example 5), and 2.0 g (0.017 moles) of pyridine hydrochloride in 85 ml of isopropanol was stirred and refluxed in an oil bath for 30 minutes. The reaction was cooled in an ice bath, and the solid was collected by filtration and washed with isopropanol, and then with ether yielding 7.26 g of crude product as the hydrochloride salt. This material was purified by chromatography of the free base on silica gel by elution with 1:39 methanol-methylene chloride.

Workup

  1. temperaturerefluxed in an oil bath for 30 minutes
  2. temperatureThe reaction was cooled in an ice bath
  3. filtrationthe solid was collected by filtration
  4. washwashed with isopropanol
  5. customThis material was purified by chromatography of the free base on silica gel by elution with 1:39 methanol-methylene chloride

Sources & evidence

ORD record
ord-c790a03db13e45478e181b583f0fbf50
Source dataset
uspto-grants-2008_07
Patent number
US07399865B2

Reaction notes

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