5-Amino-4-fluoro-2-methylphenol → HCID 22646662, compound

HRID 393579Notes

Reaction equation

HRID 393579 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.[F:20][C:21]1[CH:27]=[C:26]([CH3:28])[C:25]([OH:29])=[CH:24][C:22]=1[NH2:23]>C(O)(C)C>[ClH:2].[C:13]([C:10]1[CH:11]=[C:12]2[C:7](=[CH:8][C:9]=1[O:15][CH2:16][CH2:17][O:18][CH3:19])[N:6]=[CH:5][CH:4]=[C:3]2[NH:23][C:22]1[CH:24]=[C:25]([OH:29])[C:26]([CH3:28])=[CH:27][C:21]=1[F:20])#[N:14]

Participants

4

Reactant 2

HCID 101540985-Amino-4-fluoro-2-methylphenolHCID 22646521HCID 22646521, compound

Product 1

HCID 22646662HCID 22646662, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

4-Chloro-6-cyano-7-(2-methoxyethoxy)quinoline hydrochloride (300 mg, 1 mmol) and 2-fluoro-5-hydroxy-4-methylaniline (141 mg, 1 mmol) in isopropanol (10 ml) was heated at reflux for 2 hours. The mixture was allowed to cool, the precipitated product collected by filtration, washed with acetone and dried to give 6-cyano-4-(2-fluoro-5-hydroxy-4-methylanilino)-7-(2-methoxyethoxy)quinoline hydrochloride (273 mg, 68%).

Workup

  1. temperatureat reflux for 2 hours
  2. temperatureto cool
  3. filtrationthe precipitated product collected by filtration
  4. washwashed with acetone
  5. customdried

Sources & evidence

ORD record
ord-9f3b61b34e24458cae23a3e8e8a77a56
Source dataset
uspto-grants-2004_10
Patent number
US06809097B1

Reaction notes

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