Chlorine → N-(4-Chloro-3-cyano-7-ethoxy-6-quinolinyl)acetamide

HRID 902444Notes

Reaction equation

HRID 902444 reaction equation
[CH3:1][CH2:2][O:3][C:4]1[CH:9]=[C:8]2[NH:10][CH:11]=[C:12]([C:15]#[N:16])[C:13](=O)[C:7]2=[CH:6][C:5]=1[NH:17][C:18]([CH3:20])=[O:19].[Cl:21]Cl>>[CH3:1][CH2:2][O:3][C:4]1[CH:9]=[C:8]2[N:10]=[CH:11][C:12]([C:15]#[N:16])=[C:13]([Cl:21])[C:7]2=[CH:6][C:5]=1[NH:17][C:18]([CH3:20])=[O:19]

Participants

3

Reactant 2

HCID 24526ChlorineHCID 11459935N-(3-Cyano-7-ethoxy-4-hydroxyquinolin-6-yl)acetamide

Product 1

HCID 11358234N-(4-Chloro-3-cyano-7-ethoxy-6-quinolinyl)acetamide

Procedure

3-Cyano-7-ethoxy-4-hydroxy-6-N-acetylquinoline 6 was reacted with a chlorine-substituting reagent to yield 4-Chloro-3-cyano-7-ethoxy-6-N-acetylquinoline 7 followed by condensation with 3-chloro-4-fluoroaniline optionally in the presence of acid to yield N-[4-(3-Chloro-4-fluoro-phenylamino)-3-cyano-7-ethoxy-quinolin-6-yl]-acetamide 8.

Sources & evidence

ORD record
ord-d3dc4ff8e5884eff9e861b5c7b68fd72
Source dataset
uspto-grants-2008_04
Patent number
US07365203B2

Reaction notes

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