Stannous chloride dihydrate → 5'-Amino-2'-fluorobiphenyl-2-carbonitrile

HRID 1061737ノート

反応式

HRID 1061737 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-])=O)=[CH:4][C:3]=1[C:11]1[C:12]([C:17]#[N:18])=[CH:13][CH:14]=[CH:15][CH:16]=1.O.O.[Sn](Cl)Cl>C(O)C.O1CCCC1>[NH2:8][C:5]1[CH:6]=[CH:7][C:2]([F:1])=[C:3]([C:11]2[C:12]([C:17]#[N:18])=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:4]=1

参加物

5

反応物 2

HCID 61436Stannous chloride dihydrateHCID 114478612'-Fluoro-5'-nitrobiphenyl-2-carbonitrile

生成物 1

HCID 114699075'-Amino-2'-fluorobiphenyl-2-carbonitrile収率 75.4%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

A cooled (0° C.) suspension of 2′-fluoro-5′-nitrobiphenyl-2-carbonitrile (24.2 g, 100 mmol) in ethanol (150 ml) and tetrahydrofuran (150 ml) was treated with tin(II) chloride dihydrate (67.7 g, 300 mmol) and the mixture was stirred to ambient temperature over 12 h. The solvent was removed in vacuo and the residue treated with ice-cold 2N sodium hydroxide (750 ml). The resulting slurry was stirred for 60 min then extracted with dichloromethane (2×400 ml). The organics were combined, washed with water, brine, dried over anhydrous magnesium sulfate, filtered and concentrated to give a red solid. Crystallisation from toluene gave 5′-amino-2′-fluorobiphenyl-2-carbonitrile as a cream-coloured solid (16 g, 75%): δH (400 MHz, CDCl3) 3.65 (2H, br), 6.67-6.73 (2H, m), 7.00 (1H, t, J 9), 7.44-7.49 (2H, m), 7.64 (1H, td, J 9 and 2), 7.75 (1H, dd, J 8 and 2); m/z (ES+) 213 (M++H).

後処理

  1. temperatureA cooled
  2. customThe solvent was removed in vacuo
  3. additionthe residue treated with ice-cold 2N sodium hydroxide (750 ml)
  4. stirringThe resulting slurry was stirred for 60 min
  5. extractionthen extracted with dichloromethane (2×400 ml)
  6. washwashed with water, brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customto give a red solid
  11. customCrystallisation from toluene

出典と根拠

ORDレコード
ord-83c677ebdcf54f04a013114c871ed61e
出典データセット
uspto-grants-2005_11
特許番号
US06960598B2

反応ノート

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