5-Amino-2-chloro-4-fluorophenol → 4-(4-Chloro-2-fluoro-5-hydroxyanilino)-6-methoxy-7-(3-morpholinopropoxy)quinoline hydrochloride hydrate

HRID 393608Notes

Reaction equation

HRID 393608 reaction equation
Cl.[Cl:2][C:3]1[C:12]2[C:7](=[CH:8][C:9]([O:15][CH2:16][CH2:17][CH2:18][N:19]3[CH2:24][CH2:23][O:22][CH2:21][CH2:20]3)=[C:10]([O:13][CH3:14])[CH:11]=2)[N:6]=[CH:5][CH:4]=1.[Cl:25][C:26]1[C:32]([OH:33])=[CH:31][C:29]([NH2:30])=[C:28]([F:34])[CH:27]=1>CC(O)CCC>[OH2:13].[ClH:2].[Cl:25][C:26]1[C:32]([OH:33])=[CH:31][C:29]([NH:30][C:3]2[C:12]3[C:7](=[CH:8][C:9]([O:15][CH2:16][CH2:17][CH2:18][N:19]4[CH2:24][CH2:23][O:22][CH2:21][CH2:20]4)=[C:10]([O:13][CH3:14])[CH:11]=3)[N:6]=[CH:5][CH:4]=2)=[C:28]([F:34])[CH:27]=1

Participants

4

Reactant 2

HCID 1586545-Amino-2-chloro-4-fluorophenolHCID 226466224-Chloro-6-methoxy-7-(3-morpholinopropoxy)quinoline hydrochloride

Product 1

HCID 226466214-(4-Chloro-2-fluoro-5-hydroxyanilino)-6-methoxy-7-(3-morpholinopropoxy)quinoline hydrochloride hydrateYield 150.1%

Reagents, catalysts & solvents 1

HCID 223862-PentanolSolvent

Procedure

A solution of 4-chloro-6-methoxy-7-(3-morpholinopropoxy)quinoline hydrochloride (300 mg, 0.73 mmol), and 4-chloro-2-fluoro-5-hydroxyaniline (130 mg, 0.8 mmol), (as described in EP 61741 A2), in 2-pentanol (15 ml) was heated at reflux for 5 hours. The resulting solid was collected by filtration, washed with acetone and dried under vacuum to give 4-(4-chloro-2-fluoro-5-hydroxyanilino)-6-methoxy-7-(3-morpholinopropoxy)quinoline hydrochloride hydrate (283 mg, 73%) as a yellow solid.

Workup

  1. temperatureat reflux for 5 hours
  2. filtrationThe resulting solid was collected by filtration
  3. washwashed with acetone
  4. customdried under vacuum

Sources & evidence

ORD record
ord-c5c778aaf1ff4f3fbaf3cc5068992bbc
Source dataset
uspto-grants-2004_10
Patent number
US06809097B1

Reaction notes

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