Hydrochloric Acid → HCID 22646549, compound

HRID 393624Notes

Reaction equation

HRID 393624 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([Cl:12])=[CH:9][CH:10]=2)[N:5]=[CH:4][CH:3]=1.[F:13][C:14]1[CH:20]=[C:19]([CH3:21])[C:18]([OH:22])=[CH:17][C:15]=1[NH2:16].Cl>CC(O)CCC.C(O)(C)C>[ClH:1].[Cl:12][C:8]1[CH:7]=[C:6]2[C:11]([C:2]([NH:16][C:15]3[CH:17]=[C:18]([OH:22])[C:19]([CH3:21])=[CH:20][C:14]=3[F:13])=[CH:3][CH:4]=[N:5]2)=[CH:10][CH:9]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 68664,7-DichloroquinolineHCID 101540985-Amino-4-fluoro-2-methylphenol

Product 1

HCID 22646549HCID 22646549, compoundYield 88.4%

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 223862-PentanolSolvent

Procedure

A solution of 4,7-dichloroquinoline (198 mg, 1 mmol) and 2-fluoro-5-hydroxy-4-methylaniline (1 69 mg, 1.2 mmol), (prepared as described for the starting material in Example 1), in 2-pentanol (5 ml) containing 5M hydrochloric acid in isopropanol (0.5 ml) was heated at reflux for 2 hours. The volatiles were removed by evaporation and the residue was triturated with ether. The solid was collected by filtration, washed with isopropanol, followed by ether and dried under vacuum to give 7-chloro-4-(2-fluoro-5-hydroxy-4-methylanilino)quinoline hydrochloride (300 mg, 88%).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2 hours
  3. customThe volatiles were removed by evaporation
  4. customthe residue was triturated with ether
  5. filtrationThe solid was collected by filtration
  6. washwashed with isopropanol
  7. customdried under vacuum

Sources & evidence

ORD record
ord-afbe6977fe3144e9b7df267085e90d21
Source dataset
uspto-grants-2004_10
Patent number
US06809097B1

Reaction notes

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