5-Amino-2-chloro-4-fluorophenol → 4-(4-Chloro-2-fluoro-5-hydroxyanilino)-6-methoxy-7-(2-methoxyethoxy)quinoline hydrochloride

HRID 393631Notes

Reaction equation

HRID 393631 reaction equation
Cl.[Cl:2][C:3]1[C:12]2[C:7](=[CH:8][C:9]([O:15][CH2:16][CH2:17][O:18][CH3:19])=[C:10]([O:13][CH3:14])[CH:11]=2)[N:6]=[CH:5][CH:4]=1.[Cl:20][C:21]1[C:27]([OH:28])=[CH:26][C:24]([NH2:25])=[C:23]([F:29])[CH:22]=1>>[ClH:2].[Cl:20][C:21]1[C:27]([OH:28])=[CH:26][C:24]([NH:25][C:3]2[C:12]3[C:7](=[CH:8][C:9]([O:15][CH2:16][CH2:17][O:18][CH3:19])=[C:10]([O:13][CH3:14])[CH:11]=3)[N:6]=[CH:5][CH:4]=2)=[C:23]([F:29])[CH:22]=1

Participants

3

Reactant 2

HCID 1586545-Amino-2-chloro-4-fluorophenolHCID 226466534-Chloro-6-methoxy-7-(2-methoxyethoxy)quinoline hydrochloride

Product 1

HCID 226466034-(4-Chloro-2-fluoro-5-hydroxyanilino)-6-methoxy-7-(2-methoxyethoxy)quinoline hydrochlorideYield 67.5%

Procedure

Using an analogous procedure to that described in Example 25, 4-chloro-6-methoxy-7-(2-methoxyethoxy)quinoline hydrochloride (500 mg, 1.64 mmol), (prepared as described for the starting material in Example 5), was reacted with 4-chloro-2-fluoro-5-hydroxyaniline (270 mg, 1.64 mmol), (as described in EP 61741 A2), for 5 hours to give 4-(4-chloro-2-fluoro-5-hydroxyanilino)-6-methoxy-7-(2-methoxyethoxy)quinoline hydrochloride (475 mg, 67%).

Workup

  1. custom(prepared

Sources & evidence

ORD record
ord-491225820a5343a4878a282e8a5500f1
Source dataset
uspto-grants-2004_10
Patent number
US06809097B1

Reaction notes

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