Water → HCID 86614469, compound

HRID 639616Notes

Reaction equation

HRID 639616 reaction equation
[CH2:1]([NH:8][C:9]1[CH:14]=[C:13]([CH:15]2[CH2:17][CH2:16]2)[N:12]=[C:11]([Cl:18])[C:10]=1[N+:19]([O-])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O>CC(O)=O.[Fe]>[CH2:1]([NH:8][C:9]1[CH:14]=[C:13]([CH:15]2[CH2:16][CH2:17]2)[N:12]=[C:11]([Cl:18])[C:10]=1[NH2:19])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 962WaterHCID 86614467HCID 86614467, compound

Product 1

HCID 86614469HCID 86614469, compoundYield 98.2%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Procedure

Benzyl-(2-chloro-6-cyclopropyl-3-nitro-pyridin-4-yl)-amine (245 mg, 0.8 mmol) was dissolved in AcOH:H2O (9.0:0.9 mL). Iron powder (270 mg, 4.8 mmol) was added and the mixture was vigorously stirred at room temperature under a nitrogen atmosphere over the weekend, during which an off-white precipitate had precipitated out. The reaction mixture was diluted with EtOAc (20 mL) and water (20 mL), the mixture filtered through celite, and the filter cake washed with EtOAc (20 mL). The phases were separated and the organic layer was washed with saturated aqueous NaHCO3 (10 mL) and brine (10 mL), dried over MgSO4 and concentrated in vacuo. The residue was dried in vacuo at 40° C. overnight to give the title compound (215 mg) as an off-white crystalline solid.

Workup

  1. customhad precipitated out
  2. additionThe reaction mixture was diluted with EtOAc (20 mL) and water (20 mL)
  3. filtrationthe mixture filtered through celite
  4. washthe filter cake washed with EtOAc (20 mL)
  5. customThe phases were separated
  6. washthe organic layer was washed with saturated aqueous NaHCO3 (10 mL) and brine (10 mL)
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated in vacuo
  9. customThe residue was dried in vacuo at 40° C. overnight

Sources & evidence

ORD record
ord-2b566191fce148419bec832ee18c844f
Source dataset
uspto-grants-2010_04
Patent number
US07691877B2

Reaction notes

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