5-Amino-2-chloro-4-fluorophenol → 7-Benzyloxy-4-(4-chloro-2-fluoro-5-hydroxyanilino)-6-methoxyquinoline hydrochloride

HRID 393618Notes

Reaction equation

HRID 393618 reaction equation
Cl.[CH2:2]([O:9][C:10]1[CH:19]=[C:18]2[C:13]([C:14]([Cl:20])=[CH:15][CH:16]=[N:17]2)=[CH:12][C:11]=1[O:21][CH3:22])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[Cl:23][C:24]1[C:30]([OH:31])=[CH:29][C:27]([NH2:28])=[C:26]([F:32])[CH:25]=1>CC(O)CC>[ClH:20].[CH2:2]([O:9][C:10]1[CH:19]=[C:18]2[C:13]([C:14]([NH:28][C:27]3[CH:29]=[C:30]([OH:31])[C:24]([Cl:23])=[CH:25][C:26]=3[F:32])=[CH:15][CH:16]=[N:17]2)=[CH:12][C:11]=1[O:21][CH3:22])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 1586545-Amino-2-chloro-4-fluorophenolHCID 226465617-Benzyloxy-4-chloro-6-methoxyquinoline hydrochloride

Product 1

HCID 226465807-Benzyloxy-4-(4-chloro-2-fluoro-5-hydroxyanilino)-6-methoxyquinoline hydrochlorideYield 43.4%

Reagents, catalysts & solvents 1

HCID 6568(+-)-2-ButanolSolvent

Procedure

Using an analogous procedure to that described for the synthesis of Example 11, 7-benzyloxy-4-chloro-6-methoxyquinoline hydrochloride (336 mg, 1 mmol), (prepared as described for the starting material in Example 3), was reacted with 4-chloro-2-fluoro-5-hydroxyaniline (178 mg, 1.1 mmol), (as described in EP 61741 A2), in 2-butanol (15 ml) to give 7-benzyloxy-4-(4-chloro-2-fluoro-5-hydroxyanilino)-6-methoxyquinoline hydrochloride (200 mg, 43%).

Workup

  1. custom(prepared

Sources & evidence

ORD record
ord-56c9fa5d07f04bb58fa0391e4028b395
Source dataset
uspto-grants-2004_10
Patent number
US06809097B1

Reaction notes

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