Ammonium Chloride → HCID 68158071, compound

HRID 243266Notes

Reaction equation

HRID 243266 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([N+:15]([O-])=O)=[C:6]([NH:8][CH:9]2[CH2:12][CH:11]([C:13]#[N:14])[CH2:10]2)[CH:7]=1.[Cl-].[NH4+]>CO.O.[Fe]>[NH2:15][C:5]1[CH:4]=[CH:3][C:2]([F:1])=[CH:7][C:6]=1[NH:8][CH:9]1[CH2:10][CH:11]([C:13]#[N:14])[CH2:12]1

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 68157072HCID 68157072, compound

Product 1

HCID 68158071HCID 68158071, compoundYield 79%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 3-(5-fluoro-2-nitrophenylamino)cyclobutanecarbonitrile (0.38 g, 1.61 mmol), iron powder (0.36 g, 6.44 mmol) and ammonium chloride (0.50 g, 9.66 mmol) in methanol (10 mL) and water (4 mL) was stirred at 90° C. for 2 hours. After cooling the solid material was filtered off and the solution was concentrated in vacuo. The residue was partitioned between ethyl acetate (3×) and water, then the combined organic layers were washed with brine, dried (Na2SO4) and concentrated in vacuo to give the title compound as a dark green gum (0.26 g, 79%). LCMS (Method B): RT 1.75 min [M+H]+ 206.0

Workup

  1. temperatureAfter cooling the solid material
  2. filtrationwas filtered off
  3. concentrationthe solution was concentrated in vacuo
  4. customThe residue was partitioned between ethyl acetate (3×) and water
  5. washthe combined organic layers were washed with brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-70a8714f948d406d9853c74dc92b40ed
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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