Methanol → HCID 22646514, compound

HRID 393651Notes

Reaction equation

HRID 393651 reaction equation
Cl.[Cl:2][C:3]1[C:12]2[C:7](=[CH:8][C:9]([O:15][CH3:16])=[C:10]([C:13]#[N:14])[CH:11]=2)[N:6]=[CH:5][CH:4]=1.CO.[F:19][C:20]1[CH:26]=[C:25]([CH3:27])[C:24]([OH:28])=[CH:23][C:21]=1[NH2:22]>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][CH3:16])[N:6]=[CH:5][CH:4]=[C:3]2[NH:22][C:21]1[CH:23]=[C:24]([OH:28])[C:25]([CH3:27])=[CH:26][C:20]=1[F:19])#[N:14]

Participants

5

Reactant 3

HCID 887MethanolHCID 101540985-Amino-4-fluoro-2-methylphenolHCID 22646546HCID 22646546, compound

Product 1

HCID 22646514HCID 22646514, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of 4-chloro-6-cyano-7-methoxyquinoline hydrochloride (500 mg, 2 mmol), (prepared by an analogous procedure to that described for the starting material in Example 1 but using methanol instead of 2-methoxyethanol), and 2-fluoro-5-hydroxy-4-methylaniline (141 mg, 1 mmol), (prepared as described for the starting material in Example 1), in isopropanol (10 ml) was heated at reflux for 4 hours. The mixture was allowed to cool, the solid product was collected by filtration, washed with acetone and dried to give 6-cyano-4-(2-fluoro-5-hydroxy-4-methylanilino)-7-methoxyquinoline hydrochloride (176 mg, 54%) as a light brown solid.

Workup

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

Sources & evidence

ORD record
ord-0bebf2c78b384b728e4688fc3ad759f7
Source dataset
uspto-grants-2004_10
Patent number
US06809097B1

Reaction notes

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