Tetrahydrofuran → 4'-Trifluoromethyl-biphenyl-2-carboxylic acid (3-amino-phenyl)-amide

HRID 841838ノート

反応式

HRID 841838 の反応式
C([O-])=O.[NH4+].[N+:5]([C:8]1[CH:9]=[C:10]([NH:14][C:15]([C:17]2[C:18]([C:23]3[CH:28]=[CH:27][C:26]([C:29]([F:32])([F:31])[F:30])=[CH:25][CH:24]=3)=[CH:19][CH:20]=[CH:21][CH:22]=2)=[O:16])[CH:11]=[CH:12][CH:13]=1)([O-])=O.C1COCC1>[OH-].[OH-].[Pd+2].C(O)(C)C.C(OCC)(=O)C>[NH2:5][C:8]1[CH:9]=[C:10]([NH:14][C:15]([C:17]2[C:18]([C:23]3[CH:28]=[CH:27][C:26]([C:29]([F:30])([F:31])[F:32])=[CH:25][CH:24]=3)=[CH:19][CH:20]=[CH:21][CH:22]=2)=[O:16])[CH:11]=[CH:12][CH:13]=1

参加物

7

反応物 3

HCID 8028TetrahydrofuranHCID 2723923Ammonium formateHCID 101569574'-Trifluoromethyl-biphenyl-2-carboxylic acid (3-nitro-phenyl)-amide

生成物 1

HCID 99248284'-Trifluoromethyl-biphenyl-2-carboxylic acid (3-amino-phenyl)-amide収率 94%

試薬・触媒・溶媒 3

HCID 9942167Palladium hydroxide触媒HCID 3776Isopropanol溶媒HCID 8857Ethyl Acetate溶媒

実験手順

Ammonium formate (16.3 g, 258 mmol, 3 equiv), followed by Pearlman's catalyst [Pd(OH)2] (6.03 g, 4.30 mmol, 0.05 equiv) was added to a solution of 4′-trifluoromethyl-biphenyl-2-carboxylic acid (3-nitro-phenyl)-amide (33.2 g, 85.9 mmol, 1 equiv) in isopropanol (330 mL, 10 volumes) and ethyl acetate (170 mL, 5 volumes). The mixture was heated at reflux for 3 hours. After cooling, THF (500 mL) was added to the reaction mixture to help solubilize the product. The reaction mixture was filtered through diatomaceous earth and the filtrate was concentrated to about 100 mL. Ethyl acetate (600 mL) and THF (200 mL) were added. The organic layer was washed with saturated sodium bicarbonate solution (300 mL), dried over sodium sulfate, filtered, and concentrated to afford 4′-trifluoromethyl-biphenyl-2-carboxylic acid (3-amino-phenyl)-amide (28.7 g, 94%) as an off-white solid.

後処理

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 3 hours
  3. temperatureAfter cooling
  4. filtrationThe reaction mixture was filtered through diatomaceous earth
  5. concentrationthe filtrate was concentrated to about 100 mL
  6. additionEthyl acetate (600 mL) and THF (200 mL) were added
  7. washThe organic layer was washed with saturated sodium bicarbonate solution (300 mL)
  8. dry with materialdried over sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated

出典と根拠

ORDレコード
ord-7a7527c6641c4d2699f631b6696b603a
出典データセット
uspto-grants-2002_04
特許番号
US06369075B1

反応ノート

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