2-(Benzyloxy)-5-nitro-3-phenylpyridine → HCID 58415872, compound

HRID 42012Notes

Reaction equation

HRID 42012 reaction equation
[CH2:1]([O:8][C:9]1[C:14]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:13][C:12]([N+:21]([O-])=O)=[CH:11][N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(O)C.Cl.[Fe]>[CH2:1]([O:8][C:9]1[N:10]=[CH:11][C:12]([NH2:21])=[CH:13][C:14]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 1

HCID 673942112-(Benzyloxy)-5-nitro-3-phenylpyridine

Product 1

HCID 58415872HCID 58415872, compoundYield 81.2%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 2-(benzyloxy)-5-nitro-3-phenylpyridine (0.98 mmol, 0.3 g) in 10 mL of ethanol, 0.1 mL of HCl 35% and 0.27 g of Fe was added. The mixture was heated at 90° C. for 4 hours. The crude was filtered through Celite and washed with ethanol. The solvent was evaporated, ethyl acetate was added and was washed with NaHCO3 4% aqueous solution, water and brine. The crude was purified by chromatography eluting with DCM/MeOH mixtures affording 0.22 g (yield 79%) of expected product.

Workup

  1. filtrationThe crude was filtered through Celite
  2. washwashed with ethanol
  3. customThe solvent was evaporated
  4. additionethyl acetate was added
  5. washwas washed with NaHCO3 4% aqueous solution, water and brine
  6. customThe crude was purified by chromatography
  7. washeluting with DCM/MeOH

Sources & evidence

ORD record
ord-7ee7410d972e4921b333c9256dc0a28a
Source dataset
uspto-grants-2013_09
Patent number
US08536165B2

Reaction notes

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