Stannous chloride dihydrate → 5'-Amino-5,2'-difluorobiphenyl-2-carbonitrile

HRID 1167125ノート

反応式

HRID 1167125 の反応式
[F:1][C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[C:12]([N+:14]([O-])=O)[CH:11]=[CH:10][C:9]=2[F:17])[C:5]([C:18]#[N:19])=[CH:4][CH:3]=1.O.O.[Sn](Cl)Cl>O1CCCC1.C(O)C>[NH2:14][C:12]1[CH:11]=[CH:10][C:9]([F:17])=[C:8]([C:6]2[C:5]([C:18]#[N:19])=[CH:4][CH:3]=[C:2]([F:1])[CH:7]=2)[CH:13]=1

参加物

5

反応物 2

HCID 61436Stannous chloride dihydrateHCID 222852855,2'-Difluoro-5'-nitrobiphenyl-2-carbonitrile

生成物 1

HCID 222853335'-Amino-5,2'-difluorobiphenyl-2-carbonitrile

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

5,2′-Difluoro-5′-nitrobiphenyl-2-carbonitrile (3.25 g, 12.5 mmol) in tetrahydrofuran (20 ml) and ethanol (20 ml) was treated with tin(II) chloride dihydrate (9.86 g, 43.8 mmol) and the mixture left to stir at ambient temperature for 18 h. The solvent was evaporated and the residue stirred with 2 N sodium hydroxide solution (40 ml) for 2 h. The resulting suspension was diluted with water (100 ml) and extracted with dichloromethane (3×200 ml). The combined organics were washed with water (200 ml), brine (200 ml), dried over anhydrous sodium sulfate, filtered and evaporated to give the title compound as a brown solid: 1H NMR (360 MHz, CDCl3) δ 3.68 (2H, s), 6.67-6.76 (2H, m), 7.02 (1H, dd, J 9, 9 Hz), 7.12-7.27 (2H, m), 7.78 (1H, dd, J 9, 6 Hz).

後処理

  1. waitthe mixture left
  2. customThe solvent was evaporated
  3. stirringthe residue stirred with 2 N sodium hydroxide solution (40 ml) for 2 h
  4. additionThe resulting suspension was diluted with water (100 ml)
  5. extractionextracted with dichloromethane (3×200 ml)
  6. washThe combined organics were washed with water (200 ml), brine (200 ml)
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. customevaporated

出典と根拠

ORDレコード
ord-7b053053009940f29e5f7a4fac596953
出典データセット
uspto-grants-2003_09
特許番号
US06617326B2

反応ノート

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