Hydrochloric Acid → 4-(2-Fluoro-5-hydroxy-4-methylanilino)-6-methoxy-7-[2-(2-methoxyethoxy)ethoxy]cinnoline

HRID 7501Notes

Reaction equation

HRID 7501 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH2:15][CH2:16][O:17][CH2:18][CH2:19][O:20][CH3:21])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[N:4][CH:3]=1.[F:22][C:23]1[CH:29]=[C:28]([CH3:30])[C:27]([OH:31])=[CH:26][C:24]=1[NH2:25].Cl>CC(O)CCC.C(O)(C)C>[F:22][C:23]1[CH:29]=[C:28]([CH3:30])[C:27]([OH:31])=[CH:26][C:24]=1[NH:25][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH2:15][CH2:16][O:17][CH2:18][CH2:19][O:20][CH3:21])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[N:4][CH:3]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 101540985-Amino-4-fluoro-2-methylphenolHCID 219910424-Chloro-6-methoxy-7-(2-(2-methoxyethoxy)ethoxy)cinnoline

Product 1

HCID 219910364-(2-Fluoro-5-hydroxy-4-methylanilino)-6-methoxy-7-[2-(2-methoxyethoxy)ethoxy]cinnoline

Reagents, catalysts & solvents 2

HCID 3776IsopropanolCatalystHCID 223862-PentanolSolvent

Procedure

A solution of 4-chloro-6-methoxy-7-[2-(2-methoxyethoxy)ethoxy]cinnoline (130 mg, 0.41 mmol) and 2-fluoro-5-hydroxy-4-methylaniline (70 mg, 0.5 mmol), (prepared as described for the starting material in Example 11), in 2-pentanol (3 ml) containing 5M hydrogen chloride in isopropanol (2 drops) was heated at reflux for 45 minutes. After cooling the solid was filtered off, washed with isopropanol followed by ether to give 4-(2-fluoro-5-hydroxy-4-methylanilino)-6-methoxy-7-[2-(2-methoxyethoxy)ethoxy]cinnoline as an hydrochloride salt (159 mg, 88%).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 45 minutes
  3. temperatureAfter cooling the solid
  4. filtrationwas filtered off
  5. washwashed with isopropanol

Sources & evidence

ORD record
ord-b74e9513a51b49eb94d36645a0f6e775
Source dataset
uspto-grants-2006_08
Patent number
US07087602B2

Reaction notes

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