HCID 70663585, compound → HCID 68293908, compound

HRID 877995Notes

Reaction equation

HRID 877995 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][N:11]=[CH:10][C:9]=2[N+:14]([O-])=O)=[C:4]([CH3:17])[CH:3]=1>C(O)(=O)C.[Zn]>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][N:11]=[CH:10][C:9]=2[NH2:14])=[C:4]([CH3:17])[CH:3]=1

Participants

4

Reactant 1

HCID 70663585HCID 70663585, compound

Product 1

HCID 68293908HCID 68293908, compoundYield 33.1%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
70 °C

Procedure

Zinc dust (4.37 g, 66.7 mmol) was added in three portions over 15 min to 4-(4-fluoro-2-methylphenyl)-3-nitropyridine (3.1 g, 13.3 mmol) in acetic acid (30 mL). The reaction mixture was then heated to 70° C. for two hours. After cooling to room temperature, the reaction mixture was filtered through Celite and all volatiles were removed under reduced pressure. The resulting oil was suspended in EtOAc and washed with saturated aqueous NaHCO3 solution and brine. The organic phase was dried over MgSO4 and filtered. Evaporation of volatiles under reduced pressure gave the crude product which was purified by flash chromatography (EtOAc) to yield the desired compound (890 mg, 33%). The material was used in the next step without further purification.

Workup

  1. temperatureAfter cooling to room temperature
  2. filtrationthe reaction mixture was filtered through Celite
  3. customall volatiles were removed under reduced pressure
  4. washwashed with saturated aqueous NaHCO3 solution and brine
  5. dry with materialThe organic phase was dried over MgSO4
  6. filtrationfiltered
  7. customEvaporation of volatiles under reduced pressure
  8. customgave the crude product which
  9. customwas purified by flash chromatography (EtOAc)

Sources & evidence

ORD record
ord-467df2c6e66f4847b8df99fec9ebd7b4
Source dataset
uspto-grants-2015_03
Patent number
US08987307B2

Reaction notes

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