5-Amino-2-chloro-4-fluorophenol → 4-(4-Bromo-2-fluoro-5-hydroxyanilino)-6,7-dimethoxyquinoline

HRID 393625Notes

Reaction equation

HRID 393625 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][CH:3]=1.[Br:16][C:17]1[C:23]([OH:24])=[CH:22][C:20]([NH2:21])=[C:19]([F:25])[CH:18]=1.ClC1C(O)=CC(N)=C(F)C=1>CC(O)CCC>[Br:16][C:17]1[C:23]([OH:24])=[CH:22][C:20]([NH:21][C:2]2[C:11]3[C:6](=[CH:7][C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=3)[N:5]=[CH:4][CH:3]=2)=[C:19]([F:25])[CH:18]=1

Participants

5

Reactant 3

HCID 1586545-Amino-2-chloro-4-fluorophenolHCID 4596104-Chloro-6,7-dimethoxyquinolineHCID 109656515-Amino-2-bromo-4-fluorophenol

Product 1

HCID 179389704-(4-Bromo-2-fluoro-5-hydroxyanilino)-6,7-dimethoxyquinolineYield 63.6%

Reagents, catalysts & solvents 1

HCID 223862-PentanolSolvent

Procedure

A suspension of 4-chloro-6,7-dimethoxyquinoline (200 mg, 0.9 mmol), (prepared as described for the starting material in Example 2), and 4-bromo-2-fluoro-5-hydroxyaniline (206 mg, 1 mmol), as described in EP 61741 A2), in 2-pentanol (8 ml) was heated at reflux for 4 hours. The precipitate was collected by filtration, washed with isopropanol, followed by ether, and dried under vacuum to give 4-(4-bromo-2-fluoro-5-hydroxyanilino)-6,7-dimethoxyquinoline (225 mg, 58%).

Workup

  1. custom(prepared
  2. temperaturewas heated
  3. temperatureat reflux for 4 hours
  4. filtrationThe precipitate was collected by filtration
  5. washwashed with isopropanol
  6. customdried under vacuum

Sources & evidence

ORD record
ord-d3b48e37b7f647fb9da5f4414da149fb
Source dataset
uspto-grants-2004_10
Patent number
US06809097B1

Reaction notes

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