HCID 72297485, compound → HCID 59432593, compound

HRID 506772Notes

Reaction equation

HRID 506772 reaction equation
[CH3:1][O:2][C:3]1[C:8]([O:9][CH3:10])=[CH:7][C:6]([N+]([O-])=O)=[C:5]([CH:14]=[CH:15][N+:16]([O-])=O)[N:4]=1>[Fe].C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[N:4]=[C:5]2[CH:14]=[CH:15][NH:16][C:6]2=[CH:7][C:8]=1[O:9][CH3:10]

Participants

4

Reactant 1

HCID 72297485HCID 72297485, compound

Product 1

HCID 59432593HCID 59432593, compoundYield 46%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 1140TolueneSolvent

Procedure

Heat a mixture of 2,3-dimethoxy-5-nitro-6-(2-nitrovinyl)pyridine, 8 (144 mg, 0.565 nmmol), Fe (0.6 g, 0.565 nmmol), SiO2 (0.565 g) under reflux in ACOH (3.4 mL) and toluene (5.7 mL). After 1 h, leave the reaction medium to cool to room temperature. Filter the reaction mixture and wash the solid with CH2Cl2 and discard. Then wash the filtrate with aqueous Na2SO3 at 1%/Na2S2O5, then with saturated NaHCO3, dry (MgSO4) and concentrate under vacuum. Purify the raw product by flash chromatography (EtOAc at 40%/heptane) to give 9 (46 mg, 46%) as a fawn-colored solid: 1H NMR (CDCl3) δ 8.04 (s broad, 1H), 7.19 (m, 1H), 7.12 (s, 1H), 6.55 (m, 1H), 4.09 (s, 3H), 3.90 (s, 3H); Rf (EtOAc at 40%/heptane)=0.10; m/z obs.=178.94 (M+1).

Workup

  1. temperatureHeat
  2. customleave
  3. customthe reaction medium
  4. filtrationFilter the reaction mixture
  5. washwash the solid with CH2Cl2 and discard
  6. washThen wash the filtrate with aqueous Na2SO3 at 1%/Na2S2O5
  7. dry with materialwith saturated NaHCO3, dry (MgSO4)
  8. concentrationconcentrate under vacuum
  9. customPurify the raw product by flash chromatography (EtOAc at 40%/heptane)

Sources & evidence

ORD record
ord-57f3e3aebd2d467f8137d68f37507b80
Source dataset
uspto-grants-2010_08
Patent number
US07786114B2

Reaction notes

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