4-Chloro-2-fluoroaniline → 7-Benzyloxy-4-(4-chloro-2-fluoroanilino)-6-methoxyquinoline hydrochloride

HRID 393645Notes

Reaction equation

HRID 393645 reaction equation
Cl.[CH2:2]([O:9][C:10]1[CH:19]=[C:18]2[C:13]([C:14]([Cl:20])=[CH:15][CH:16]=[N:17]2)=[CH:12][C:11]=1[O:21][CH3:22])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[Cl:23][C:24]1[CH:30]=[CH:29][C:27]([NH2:28])=[C:26]([F:31])[CH:25]=1>C1CCCCC1>[ClH:20].[CH2:2]([O:9][C:10]1[CH:19]=[C:18]2[C:13]([C:14]([NH:28][C:27]3[CH:29]=[CH:30][C:24]([Cl:23])=[CH:25][C:26]=3[F:31])=[CH:15][CH:16]=[N:17]2)=[CH:12][C:11]=1[O:21][CH3:22])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 938984-Chloro-2-fluoroanilineHCID 226465617-Benzyloxy-4-chloro-6-methoxyquinoline hydrochloride

Product 1

HCID 226465997-Benzyloxy-4-(4-chloro-2-fluoroanilino)-6-methoxyquinoline hydrochlorideYield 21%

Reagents, catalysts & solvents 1

HCID 8078CyclohexaneSolvent

Procedure

A mixture of 7-benzyloxy-4-chloro-6-methoxyquinoline hydrochloride (300 mg, 0.89 mmol), (prepared as described for the starting material in Example 3), and 4-chloro-2-fluoroaniline (160 mg, 1.1 mmol) was heated at reflux in cyclohexane (20 ml) for 24 hours. The solvent was removed by evaporation and the residue was triturated with ether. The solid crude product was collected by filtration and purified by column chromatography eluting with methylene chloride/methanol (100/0 increasing to 95/5) to give 7-benzyloxy-4-(4-chloro-2-fluoroanilino)-6-methoxyquinoline hydrochloride (83 mg, 21%).

Workup

  1. custom(prepared
  2. temperaturewas heated
  3. customThe solvent was removed by evaporation
  4. customthe residue was triturated with ether
  5. filtrationThe solid crude product was collected by filtration
  6. custompurified by column chromatography
  7. washeluting with methylene chloride/methanol (100/0 increasing to 95/5)

Sources & evidence

ORD record
ord-bccfd38920fb4804ae64bc79f0f9d1f2
Source dataset
uspto-grants-2004_10
Patent number
US06809097B1

Reaction notes

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