Hydrochloric Acid → 7-[(4'-Trifluoromethyl-biphenyl-2-carbonyl)-amino)-quinoline-3-carboxylic acid

HRID 431367Notes

Reaction equation

HRID 431367 reaction equation
[CH:1]([C:3]1[CH:4]=[N:5][C:6]2[C:11]([CH:12]=1)=[CH:10][CH:9]=[C:8]([NH:13][C:14]([C:16]1[C:17]([C:22]3[CH:27]=[CH:26][C:25]([C:28]([F:31])([F:30])[F:29])=[CH:24][CH:23]=3)=[CH:18][CH:19]=[CH:20][CH:21]=1)=[O:15])[CH:7]=2)=[O:2].P([O-])(O)(O)=[O:33].[K+].Cl([O-])=O.[Na+].S([O-])([O-])=O.[Na+].[Na+].Cl>C(#N)C>[F:30][C:28]([F:31])([F:29])[C:25]1[CH:24]=[CH:23][C:22]([C:17]2[C:16]([C:14]([NH:13][C:8]3[CH:7]=[C:6]4[C:11]([CH:12]=[C:3]([C:1]([OH:33])=[O:2])[CH:4]=[N:5]4)=[CH:10][CH:9]=3)=[O:15])=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:27][CH:26]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 24437Sodium SulfiteHCID 516951Monobasic potassium phosphateHCID 102022794'-Trifluoromethyl-biphenyl-2-carboxylic acid (3-formyl-quinolin-7-yl)-amideHCID 23668197Sodium Chlorite

Product 1

HCID 102967197-[(4'-Trifluoromethyl-biphenyl-2-carbonyl)-amino)-quinoline-3-carboxylic acidYield 80%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 4′-trifluoromethyl-biphenyl-2-carboxylic acid (3-formyl-quinolin-7-yl)-amide (7.65 g, 18.2 mmol, 1 equiv) in acetonitrile (100 mL, 15 volumes) was added an aqueous solution of potassium dihydrogen phosphate (1.25 M, 72.8 mL, 91 mmol, 5 equiv), followed by sodium chlorite (6.17 g, 54.6 mmol, 3 equiv). The slurry was stirred at room temperature for 12 hours. An aqueous solution of sodium sulfite (1 M, 75 mL, 75 mmol, 4.1 equiv) was added and the resulting slurry was stirred at room temperature for 15 minutes. 1 N HCl (50 mL) was added to bring the pH to about 3 to 4. The aqueous layer was extracted with ethyl acetate (2×100 mL). The combined organic layers were dried over sodium sulfate and concentrated to about 75 mL of ethyl acetate. Hexanes (about 75 mL) was added to the slurry and the resulting slurry was allowed to stir at room temperature for 2 hours. The precipitate was collected by filtration to provide 7-[(4′-trifluoromethyl-biphenyl-2-carbonyl)-amino]-quinoline-3-carboxylic acid (6.32 g, 80% over two steps) as a yellow powder.

Workup

  1. stirringthe resulting slurry was stirred at room temperature for 15 minutes
  2. extractionThe aqueous layer was extracted with ethyl acetate (2×100 mL)
  3. dry with materialThe combined organic layers were dried over sodium sulfate
  4. concentrationconcentrated to about 75 mL of ethyl acetate
  5. additionHexanes (about 75 mL) was added to the slurry
  6. stirringto stir at room temperature for 2 hours
  7. filtrationThe precipitate was collected by filtration

Sources & evidence

ORD record
ord-0280f70b87e045d2b14a6462cc45fb9d
Source dataset
uspto-grants-2003_12
Patent number
US06657065B2

Reaction notes

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