Methanol → HCID 22596370, compound

HRID 242905Notes

Reaction equation

HRID 242905 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[NH:10][C:11]1[CH:12]=[C:13]([CH:16]=[CH:17][CH:18]=1)[C:14]#[N:15])([O-])=O.CO.[NH4+].[Cl-]>[Fe].O>[NH2:1][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[NH:10][C:11]1[CH:12]=[C:13]([CH:16]=[CH:17][CH:18]=1)[C:14]#[N:15]

Participants

6

Reactant 3

HCID 887MethanolHCID 25517Ammonium ChlorideHCID 9283383HCID 9283383, compound

Product 1

HCID 22596370HCID 22596370, compoundYield 11%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Procedure

To a mixture of 3-(2-nitrophenylamino)benzonitrile (2.0 g, 8.40 mmol) in a 3:1 mixture MeOH:water (120 mL) were added NH4Cl (2.70 g, 0.05 mol) and iron powder (1.88 g, 0.03 mol) and the reaction mixture heated at reflux temperature for 1 h. After cooling to RT, the solid was filtered through a pad of Celite® and washed with additional MeOH. The filtrate was concentrated in vacuo and the resulting residue partitioned between DCM and water. The aqueous phase was further extracted with DCM (×3) and the combined organic fractions were washed with brine, dried (Na2SO4) and concentrated in vacuo. The resulting residue was purified by column chromatography (Si—PCC, gradient 0-2% MeOH in DCM) to afford the title compound as a yellow solid (185 mg, 11%). LCMS (Method J): RT 2.99 min [M+H]+ 210.0.

Workup

  1. temperaturethe reaction mixture heated
  2. temperatureat reflux temperature for 1 h
  3. filtrationthe solid was filtered through a pad of Celite®
  4. washwashed with additional MeOH
  5. concentrationThe filtrate was concentrated in vacuo
  6. customthe resulting residue partitioned between DCM and water
  7. extractionThe aqueous phase was further extracted with DCM (×3)
  8. washthe combined organic fractions were washed with brine
  9. dry with materialdried (Na2SO4)
  10. concentrationconcentrated in vacuo
  11. customThe resulting residue was purified by column chromatography (Si—PCC, gradient 0-2% MeOH in DCM)

Sources & evidence

ORD record
ord-edfdef7ae95d493e94f5578f90be6768
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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