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

HRID 2228937ノート

反応式

HRID 2228937 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 solublize 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-196049706728420f9b3395c4ae10ba14
出典データセット
uspto-grants-2002_07
特許番号
US06417367B1

反応ノート

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