Isopropanol → 4-(4-Chloro-2-fluoro-5-hydroxyanilino)-6-methoxy-7-(4-pyridylmethoxy)cinnoline

HRID 7475

Reaction equation

HRID 7475 reaction equation
Cl.Cl[C:3]1[C:12]2[C:7](=[CH:8][C:9]([O:15][CH2:16][C:17]3[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=3)=[C:10]([O:13][CH3:14])[CH:11]=2)[N:6]=[N:5][CH:4]=1.[Cl:23][C:24]1[C:30]([OH:31])=[CH:29][C:27]([NH2:28])=[C:26]([F:32])[CH:25]=1.C(O)(C)C>CC(O)CCC>[Cl:23][C:24]1[C:30]([OH:31])=[CH:29][C:27]([NH:28][C:3]2[C:12]3[C:7](=[CH:8][C:9]([O:15][CH2:16][C:17]4[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=4)=[C:10]([O:13][CH3:14])[CH:11]=3)[N:6]=[N:5][CH:4]=2)=[C:26]([F:32])[CH:25]=1

Participants

5

Reactant 3

HCID 3776IsopropanolHCID 1586545-Amino-2-chloro-4-fluorophenolHCID 219910114-Chloro-6-methoxy-7-(4-pyridylmethoxy)cinnoline hydrochloride

Product 1

HCID 219910264-(4-Chloro-2-fluoro-5-hydroxyanilino)-6-methoxy-7-(4-pyridylmethoxy)cinnoline

Reagents, catalysts & solvents 1

HCID 223862-PentanolSolvent

Procedure

A suspension of 4-chloro-6-methoxy-7-(4-pyridylmethoxy)cinnoline hydrochloride (0.17 g, 0.45 mmol) and 4-chloro-2-fluoro-5-hydroxyaniline (102 mg, 0.63 mmol), (prepared as described in EP 061741 A2), in 2-pentanol (3.5 ml) was heated at reflux overnight. After cooling, isopropanol was added. The solid formed was filtered off, washed with isopropanol, ether and dried under vacuum to give 4-(4-chloro-2-fluoro-5-hydroxyanilino)-6-methoxy-7-(4-pyridylmethoxy)cinnoline as the hydrochloride salt (yellow solid, 194 mg, 86%).

Workup

  1. temperaturewas heated
  2. temperatureat reflux overnight
  3. temperatureAfter cooling
  4. customThe solid formed
  5. filtrationwas filtered off
  6. washwashed with isopropanol, ether
  7. customdried under vacuum

Sources & evidence

ORD record
ord-0d9c8fe8bd4f4677b9f2be711a09a26f
Source dataset
uspto-grants-2006_08
Patent number
US07087602B2

Linked notes

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