Ammonium Chloride → 4',5'-Diamino-2'-fluorobiphenyl-4-carbonitrile

HRID 1424218Notes

Reaction equation

HRID 1424218 reaction equation
[NH2:1][C:2]1[C:7]([N+:8]([O-])=O)=[CH:6][C:5]([C:11]2[CH:16]=[CH:15][C:14]([C:17]#[N:18])=[CH:13][CH:12]=2)=[C:4]([F:19])[CH:3]=1.[Cl-].[NH4+]>CO.[Zn]>[NH2:1][C:2]1[C:7]([NH2:8])=[CH:6][C:5]([C:11]2[CH:12]=[CH:13][C:14]([C:17]#[N:18])=[CH:15][CH:16]=2)=[C:4]([F:19])[CH:3]=1

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 866991314'-Amino-2'-fluoro-5'-nitrobiphenyl-4-carbonitrile

Product 1

HCID 866990294',5'-Diamino-2'-fluorobiphenyl-4-carbonitrileYield 99%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 887MethanolSolvent

Procedure

To a mixture of 4′-amino-2′-fluoro-5′-nitrobiphenyl-4-carbonitrile (Preparation 90, 0.5 g, 2 mmol) and zinc dust (0.78 g, 12 mmol) in methanol (10 mL) was added ammonium chloride (0.41 g, 8 mmol) and the reaction was stirred at room temperature for 3 hours. The reaction was filtered through celite washing through with methanol (40 mL). The filtrate was concentrated to afford a solid that was purified using silica gel column chromatography eluting with EtOAc:heptanes 1:1 to afford the title compound as a brown solid (0.45 g, 99%).

Workup

  1. filtrationThe reaction was filtered through celite
  2. washwashing through with methanol (40 mL)
  3. concentrationThe filtrate was concentrated
  4. customto afford a solid
  5. customthat was purified
  6. washeluting with EtOAc:heptanes 1:1

Sources & evidence

ORD record
ord-08a34fe16450434993d349b60e5c6014
Source dataset
uspto-grants-2015_01
Patent number
US08927587B2

Reaction notes

Loading…