5-Amino-2-chloro-4-fluorophenol → HCID 22646637, compound

HRID 393586Notes

Reaction equation

HRID 393586 reaction equation
[Cl:1][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.[Cl:16][C:17]1[C:23]([OH:24])=[CH:22][C:20]([NH2:21])=[C:19]([F:25])[CH:18]=1>CC(O)CCC>[ClH:1].[Cl: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

4

Reactant 2

HCID 1586545-Amino-2-chloro-4-fluorophenolHCID 4596104-Chloro-6,7-dimethoxyquinoline

Product 1

HCID 22646637HCID 22646637, compoundYield 67.4%

Reagents, catalysts & solvents 1

HCID 223862-PentanolSolvent

Conditions

Temperature
120 °C

Procedure

A suspension of 4-chloro-6,7-dimethoxyquinoline (0.2 g, 0.89 mmol) and 4-chloro-2-fluoro-5-hydroxyaniline (173 mg, 1 mmol), (as described in EP 61741 A2), in 2-pentanol (2.5 ml) was heated at 120° C. for 6 hours. The resulting solid was collected by filtration, washed with isopropanol and then ether and dried under vacuum to give 4-(4-chloro-2-fluoro-5-hydroxyanilino)-6,7-dimethoxyquinoline hydrochloride (231 mg, 67%) as a white solid.

Workup

  1. filtrationThe resulting solid was collected by filtration
  2. washwashed with isopropanol
  3. dry with materialether and dried under vacuum

Sources & evidence

ORD record
ord-962a95ccc4d946aeaff41575d2c1c328
Source dataset
uspto-grants-2004_10
Patent number
US06809097B1

Reaction notes

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