4-Chloro-2-fluoroaniline → HCID 22646647, compound

HRID 393656Notes

Reaction equation

HRID 393656 reaction equation
Cl.[Cl:2][C:3]1[C:12]2[C:7](=[CH:8][C:9]([O:15][CH2:16][CH2:17][O:18][CH3:19])=[C:10]([C:13]#[N:14])[CH:11]=2)[N:6]=[CH:5][CH:4]=1.[Cl:20][C:21]1[CH:27]=[CH:26][C:24]([NH2:25])=[C:23]([F:28])[CH:22]=1>C(O)(C)C>[ClH:2].[Cl:20][C:21]1[CH:27]=[CH:26][C:24]([NH:25][C:3]2[C:12]3[C:7](=[CH:8][C:9]([O:15][CH2:16][CH2:17][O:18][CH3:19])=[C:10]([C:13]#[N:14])[CH:11]=3)[N:6]=[CH:5][CH:4]=2)=[C:23]([F:28])[CH:22]=1

Participants

4

Reactant 2

HCID 938984-Chloro-2-fluoroanilineHCID 22646521HCID 22646521, compound

Product 1

HCID 22646647HCID 22646647, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of 4-chloro-6-cyano-7-(2-methoxyethoxy)quinoline hydrochloride (300 mg 1 mmol), (prepared as described for the starting material in Example 1), and 4-chloro-2-fluoroaniline (0.5 ml, 3.4 mmol) in isopropanol (20 ml) was heated at reflux for 3 hours. The mixture was allowed to cool, the solid product was collected by filtration, washed with acetone and dried to give 4-(4-chloro-2-fluoroanilino)-6-cyano-7-(2-methoxyethoxy)quinoline hydrochloride (400 mg, 98%).

Workup

  1. custom(prepared
  2. temperaturewas heated
  3. temperatureat reflux for 3 hours
  4. temperatureto cool
  5. filtrationthe solid product was collected by filtration
  6. washwashed with acetone
  7. customdried

Sources & evidence

ORD record
ord-f93f4c12fafb43d6b73a266bd3916976
Source dataset
uspto-grants-2004_10
Patent number
US06809097B1

Reaction notes

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