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

HRID 51977ノート

反応式

HRID 51977 の反応式
[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

参加物

7

反応物 5

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-7ef855f7725a4deabcc675d12fe795ac
出典データセット
uspto-grants-2004_03
特許番号
US06713489B2

反応ノート

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