Stannous chloride dihydrate → HCID 22473529, compound

HRID 2183895Notes

Reaction equation

HRID 2183895 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([C:14]#[N:15])=[CH:10][CH:11]=[CH:12][CH:13]=2)=[CH:4][C:3]=1[N+:16]([O-])=O.O.O.[Sn](Cl)Cl>C(O)C.O1CCCC1>[NH2:16][C:3]1[CH:4]=[C:5]([C:8]2[C:9]([C:14]#[N:15])=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:6]=[CH:7][C:2]=1[F:1]

Participants

5

Reactant 2

HCID 61436Stannous chloride dihydrateHCID 22473582HCID 22473582, compound

Product 1

HCID 22473529HCID 22473529, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A cooled (0° C.) suspension of crude 4′-fluoro-3′-nitrobiphenyl-2-carbonitrile (10.7 g, 44 mmol) in ethanol (80 ml) and tetrahydrofuran (80 ml) was treated with tin(II) chloride dihydrate (29.8 g, 132 mmol) and this mixture was stirred at ambient temperature for 12 h. The solvent was removed in vacuo and the residue treated with ice-cold 2N sodium hydroxide (400 ml). The resulting slurry was stirred at ambient temperature 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 pre-adsorbed onto silica. Purification by chromatography on silica gel eluting with isohexane on a gradient of ethyl acetate (5-40%) gave 3′-amino-4′-fluorobiphenyl-2-carbonitrile as a cream-coloured solid (4.3 g, 46% over 2 steps): δH (400 MHz, CDCl3) 3.85 (2H, br), 6.84 (1H, ddd, J 8, 4 and 2), 6.95 (1H, dd, J 8 and 2), 7.07 (1H, dd, J 11 and 8), 7.40-7.46 (2H, m), 7.57-7.62 (1H, m), 7.72-7.74 (1H, m).

Workup

  1. temperatureA cooled
  2. customThe solvent was removed in vacuo
  3. additionthe residue treated with ice-cold 2N sodium hydroxide (400 ml)
  4. stirringThe resulting slurry was stirred at ambient temperature 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 and pre-adsorbed onto silica
  9. customPurification by chromatography on silica gel eluting with isohexane on a gradient of ethyl acetate (5-40%)

Sources & evidence

ORD record
ord-58206f07428648c7a34da88f529df948
Source dataset
uspto-grants-2005_05
Patent number
US06900215B2

Reaction notes

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