Hydrochloric Acid → 4-(4-(((4-Fluoroanilino)carbonyl)amino)phenoxy)-7-methoxy-6-quinolinecarboxylic acid

HRID 1010280Notes

Reaction equation

HRID 1010280 reaction equation
CO.[OH-].[Na+].C[O:6][C:7]([C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][C:18]=1[O:19][CH3:20])[N:15]=[CH:14][CH:13]=[C:12]2[O:21][C:22]1[CH:27]=[CH:26][C:25]([NH:28][C:29]([NH:31][C:32]2[CH:37]=[CH:36][C:35]([F:38])=[CH:34][CH:33]=2)=[O:30])=[CH:24][CH:23]=1)=[O:8].Cl>O>[F:38][C:35]1[CH:34]=[CH:33][C:32]([NH:31][C:29]([NH:28][C:25]2[CH:26]=[CH:27][C:22]([O:21][C:12]3[C:11]4[C:16](=[CH:17][C:18]([O:19][CH3:20])=[C:9]([C:7]([OH:8])=[O:6])[CH:10]=4)[N:15]=[CH:14][CH:13]=3)=[CH:23][CH:24]=2)=[O:30])=[CH:37][CH:36]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887Methanol2×HCID 14798Sodium HydroxideHCID 22936678Methyl-4-(4-(((4-fluoroanilino)carbonyl)amino)phenoxy)-7-methoxy-6-quinoline carboxylate

Product 1

HCID 229363504-(4-(((4-Fluoroanilino)carbonyl)amino)phenoxy)-7-methoxy-6-quinolinecarboxylic acidYield 78.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

After adding methanol (9 ml) and 2N aqueous sodium hydroxide (3 ml) to methyl-4-(4-(((4-fluoroanilino)carbonyl)amino)phenoxy)-7-methoxy-6-quinoline carboxylate (300 mg, 0.65 mmol), the mixture was stirred at room temperature for 2 hours and then at 60° C. for 20 minutes. The reaction solution was cooled to room temperature and 1N hydrochloric acid was added for neutralization, after which methanol (6 ml) and water (6 ml) were added, the mixture was stirred overnight, and the precipitated light brown crystals were filtered out and dried under reduced pressure to obtain the title compound (227 mg, 0.51 mmol, 78.0%).

Workup

  1. waitat 60° C. for 20 minutes
  2. temperatureThe reaction solution was cooled to room temperature
  3. stirringthe mixture was stirred overnight
  4. filtrationthe precipitated light brown crystals were filtered out
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-098a8137177a44da8402a3684c07fba1
Source dataset
uspto-grants-2011_07
Patent number
US07973160B2

Reaction notes

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