HCID 86699132, compound → HCID 86699039, compound

HRID 1424219Notes

Reaction equation

HRID 1424219 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]#[N:15])=[CH:10][C:9]=2[F:16])=[CH:4][C:3]=1[N+:17]([O-])=O>CC(O)=O.C1COCC1.[Zn]>[NH2:17][C:3]1[CH:4]=[C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]#[N:15])=[CH:10][C:9]=2[F:16])[CH:6]=[CH:7][C:2]=1[NH2:1]

Participants

4

Reactant 1

HCID 86699132HCID 86699132, compound

Product 1

HCID 86699039HCID 86699039, compoundYield 57%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 23444217Acetic acid tetrahydrofuranSolvent

Procedure

To a suspension of 4′-amino-2-fluoro-3′-nitrobiphenyl-4-carbonitrile (Preparation 92, 3 g, 11.66 mmol) in AcOH/THF (70 mL/70 mL) was added zinc dust (6.9 g, 105.6 mmol) and the reaction stirred at room temperature for 18 hours. The reaction was filtered and the filtrate concentrated in vacuo. The residue was treated with saturated aqueous NaHCO3 solution (200 mL) and extracted with EtOAc (200 mL). The organic layer was collected, dried over Na2SO4 and concentrated in vacuo. The solid was triturated with MTBE (30 mL) and filtered to afford the title compound as a brown solid (1.5 g, 57%).

Workup

  1. filtrationThe reaction was filtered
  2. concentrationthe filtrate concentrated in vacuo
  3. additionThe residue was treated with saturated aqueous NaHCO3 solution (200 mL)
  4. extractionextracted with EtOAc (200 mL)
  5. customThe organic layer was collected
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated in vacuo
  8. customThe solid was triturated with MTBE (30 mL)
  9. filtrationfiltered

Sources & evidence

ORD record
ord-5736bbd319be4d73b786673dd5216c91
Source dataset
uspto-grants-2015_01
Patent number
US08927587B2

Reaction notes

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