5-Amino-4-fluoro-2-methylphenol → HCID 22646552, compound

HRID 393649Notes

Reaction equation

HRID 393649 reaction equation
Cl.[Cl:2][C:3]1[C:12]2[C:7](=[CH:8][C:9]([O:15][CH3:16])=[C:10]([O:13][CH3:14])[CH:11]=2)[N:6]=[CH:5][CH:4]=1.[F:17][C:18]1[CH:24]=[C:23]([CH3:25])[C:22]([OH:26])=[CH:21][C:19]=1[NH2:20]>C(O)(C)C>[ClH:2].[CH3:14][O:13][C:10]1[CH:11]=[C:12]2[C:7](=[CH:8][C:9]=1[O:15][CH3:16])[N:6]=[CH:5][CH:4]=[C:3]2[NH:20][C:19]1[CH:21]=[C:22]([OH:26])[C:23]([CH3:25])=[CH:24][C:18]=1[F:17]

Participants

4

Reactant 2

HCID 101540985-Amino-4-fluoro-2-methylphenolHCID 226465434-Chloro-6,7-dimethoxyquinoline hydrochloride

Product 1

HCID 22646552HCID 22646552, compoundYield 29%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of 4-chloro-6,7-dimethoxyquinoline hydrochloride (360 mg, 1.4 mmol), (prepared as described for the starting material in Example 2), and 2-fluoro-5-hydroxy-4-methylaniline (212 mg 1.5 mmol), (prepared as described for the starting material in Example 1), in isopropanol (15 ml) was heated at reflux for 3 hours. The mixture was allowed to cool and the solid product was collected by filtration, washed with acetone and dried to give 6,7-dimethoxy-4-(2-fluoro-5-hydroxy-4-methylanilino)quinoline hydrochloride (146 mg, 29%).

Workup

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

Sources & evidence

ORD record
ord-11f7266b6b344d93932fac6eda9d03ca
Source dataset
uspto-grants-2004_10
Patent number
US06809097B1

Reaction notes

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