Hydrochloric Acid → HCID 22646589, compound

HRID 393619Notes

Reaction equation

HRID 393619 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH2:15][CH2:16][CH2:17][C:18]3[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=3)=[C:9](OC)[CH:10]=2)[N:5]=[CH:4][CH:3]=1.[Cl:24][C:25]1[C:31]([OH:32])=[CH:30][C:28]([NH2:29])=[C:27]([F:33])[CH:26]=1.Cl.CN([CH:38]=[O:39])C>CC(O)CCC.C(O)(C)C>[Cl:24][C:25]1[C:31]([OH:32])=[CH:30][C:28]([NH:29][C:2]2[C:11]3[C:6](=[CH:7][C:8]([O:14][CH2:15][CH2:16][CH2:17][C:18]4[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=4)=[CH:9][CH:10]=3)[N:5]=[C:4]([O:39][CH3:38])[CH:3]=2)=[C:27]([F:33])[CH:26]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 1586545-Amino-2-chloro-4-fluorophenolHCID 22646612HCID 22646612, compound

Product 1

HCID 22646589HCID 22646589, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 223862-PentanolSolvent

Procedure

To a suspension of 4-chloro-6-methoxy-7-(3-(3-pyridyl)propoxy)quinoline (150 mg, 0.46 mmol) in 2-pentanol (5 ml) was added 4-chloro-2-fluoro-5-hydroxyaniline (91 mg, 0.55 mmol), (as described in EP 61741 A2), and 5M hydrogen chloride in isopropanol (0.1 ml). The mixture was heated at reflux for 15 minutes and DMF (3 ml) was added. The mixture was heated at reflux for 5 hours and the volatiles were removed by evaporation. The residue was triturated with isopropanol, collected by filtration and dried under vacuum to give 4-(4-chloro-2-fluoro-5-hydroxyanilino)-methoxy-7-(3-(3-pyridyl)propoxy)quinoline (150 mg, 62%).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 15 minutes
  3. temperatureThe mixture was heated
  4. temperatureat reflux for 5 hours
  5. customthe volatiles were removed by evaporation
  6. customThe residue was triturated with isopropanol
  7. filtrationcollected by filtration
  8. customdried under vacuum

Sources & evidence

ORD record
ord-84095f16e2ca4c1483c5193b13d68401
Source dataset
uspto-grants-2004_10
Patent number
US06809097B1

Reaction notes

Loading…