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

HRID 1167125노트

반응식

HRID 1167125 반응식
[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

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 702Ethanol용매HCID 8028Tetrahydrofuran용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-7b053053009940f29e5f7a4fac596953
출처 데이터셋
uspto-grants-2003_09
특허 번호
US06617326B2

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