Ammonium Chloride → HCID 68157539, compound

HRID 243246Notes

Reaction equation

HRID 243246 reaction equation
[F:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([NH:10][C:11]2[CH:12]=[N:13][CH:14]=[C:15]([F:17])[CH:16]=2)[C:5]([N+:18]([O-])=O)=[CH:4][CH:3]=1.[Cl-].[NH4+]>CO.O.[Fe]>[NH2:18][C:5]1[C:6]([NH:10][C:11]2[CH:12]=[N:13][CH:14]=[C:15]([F:17])[CH:16]=2)=[C:7]([C:2]([F:1])=[CH:3][CH:4]=1)[C:8]#[N:9]

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 681579506-Fluoro-2-(5-fluoropyridin-3-ylamino)-3-nitrobenzonitrile

Product 1

HCID 68157539HCID 68157539, compoundYield 61.5%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

(6-Fluoro-2-(5-fluoropyridin-3-ylamino)-3-nitrobenzonitrile (1.73 g, 6.26 mmol), iron powder (712 mg, 12.5 mmol), and ammonium chloride (966 mg, 18.8 mmol) in methanol (40 mL) and water (12 mL) were heated at 90° C. for 1 h. The reaction mixture was filtered and the filtrate concentrated in vacuo. The residue was dissolved in water and extracted with EtOAc (3×20 mL). The combined organic extracts were washed with brine, dried (MgSO4) and concentrated in vacuo. The resultant residue was subjected to flash chromatography (SiO2, eluting with 0-100% EtOAc in cyclohexane) to yield the title compound as brown solid (948 mg, 61%). 1H NMR 400 MHz δ (CDCl3): 8.05 (1H, d, J=2.4 Hz), 8.03-7.99 (1H, m), 7.01 (1H, d, J=2.1 Hz), 6.99 (1H, s), 6.59 (1H, dt, J=10.2, 2.4 Hz), 5.78 (1H, br s), 3.84 (2H, br s).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate concentrated in vacuo
  3. dissolutionThe residue was dissolved in water
  4. extractionextracted with EtOAc (3×20 mL)
  5. washThe combined organic extracts were washed with brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated in vacuo
  8. washThe resultant residue was subjected to flash chromatography (SiO2, eluting with 0-100% EtOAc in cyclohexane)

Sources & evidence

ORD record
ord-105bb421058b40358ce935566694de81
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

Loading…