Isopropanol → 4-(2-Fluoro-5-hydroxy-4-methylanilino)-6-methoxy-7-(2-methoxyethoxy)cinnoline

HRID 7478

Reaction equation

HRID 7478 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH2:15][CH2:16][O:17][CH3:18])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[N:4][CH:3]=1.[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>CC(O)CCC>[F:19][C:20]1[CH:26]=[C:25]([CH3:27])[C:24]([OH:28])=[CH:23][C:21]=1[NH:22][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH2:15][CH2:16][O:17][CH3:18])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[N:4][CH:3]=1

Participants

5

Reactant 3

HCID 3776IsopropanolHCID 101540985-Amino-4-fluoro-2-methylphenolHCID 107070484-Chloro-6-methoxy-7-(2-methoxyethoxy)cinnoline

Product 1

HCID 116176914-(2-Fluoro-5-hydroxy-4-methylanilino)-6-methoxy-7-(2-methoxyethoxy)cinnoline

Reagents, catalysts & solvents 1

HCID 223862-PentanolSolvent

Procedure

A suspension of 4-chloro-6-methoxy-7-(2-methoxyethoxy)cinnoline (0.2 g, 0.74 mmol), (prepared as described for the starting material in Example 2), and 2-fluoro-5-hydroxy-4-methylaniline (126 mg 0.89 mmol) in 2-pentanol (2.5 ml) was heated at reflux for 7.5 hours. After cooling, isopropanol was added and the solid was filtered off, washed with isopropanol and ether, and dried under vacuum to give 4-(2-fluoro-5-hydroxy-4-methylanilino)-6-methoxy-7-(2-methoxyethoxy)cinnoline as the hydrochloride salt (yellow solid 196 mg, 64%).

Workup

  1. custom(prepared
  2. temperaturewas heated
  3. temperatureat reflux for 7.5 hours
  4. temperatureAfter cooling
  5. filtrationthe solid was filtered off
  6. washwashed with isopropanol and ether
  7. customdried under vacuum

Sources & evidence

ORD record
ord-1d218b8eacb94ccf8ec1aaec2228ab0f
Source dataset
uspto-grants-2006_08
Patent number
US07087602B2

Linked notes

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