Acetic Acid → HCID 59437374, compound

HRID 657072Notes

Reaction equation

HRID 657072 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][O:10][C:11]2[N:16]=[C:15]([NH2:17])[C:14]([N+:18]([O-])=O)=[CH:13][CH:12]=2)=[CH:5][CH:4]=1.C(O)(=O)C>CO.[Zn]>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:9][O:10][C:11]2[N:16]=[C:15]([NH2:17])[C:14]([NH2:18])=[CH:13][CH:12]=2)=[CH:7][CH:8]=1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 59437335HCID 59437335, compound

Product 1

HCID 59437374HCID 59437374, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 887MethanolSolvent

Procedure

To a suspension of 6-({[4-(methyloxy)phenyl]methyl}oxy)-3-nitro-2-pyridineamine (4.8 g, 17.5 mmol) and zinc (11 g, 175 mmol) in methanol (200 mL) was added dropwise acetic acid (5 mL) at rt. After 0.5 h the reaction was filtered through celite and then the solvent was evaporated. The residue was partitioned between water (500 mL) and ethyl acetate (500 mL), the phases were separated and the water extracted with ethyl acetate (5×500 mL). The combined organic phases were dried, filtered and evaporated to afford 3.9 g of the title compound as a black solid (91%).

Workup

  1. filtrationAfter 0.5 h the reaction was filtered through celite
  2. customthe solvent was evaporated
  3. customThe residue was partitioned between water (500 mL) and ethyl acetate (500 mL)
  4. customthe phases were separated
  5. extractionthe water extracted with ethyl acetate (5×500 mL)
  6. customThe combined organic phases were dried
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-06408f07c2b647d3a094ff8757b03131
Source dataset
uspto-grants-2011_12
Patent number
US08071592B2

Reaction notes

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