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

HRID 51977노트

반응식

HRID 51977 반응식
[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

참가 물질

7

반응물 5

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

생성물 1

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

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-7ef855f7725a4deabcc675d12fe795ac
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06713489B2

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