Sodium Bicarbonate → HCID 72297485, compound

HRID 506771Notes

Reaction equation

HRID 506771 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([N+:17]([O-:19])=[O:18])[C:6]([CH:11](O)[CH2:12][N+:13]([O-:15])=[O:14])=[N:7][C:8]=1[O:9][CH3:10].CC([O-])=O.[Na+].C([O-])(O)=O.[Na+]>CC(OC(C)=O)=O>[CH3:10][O:9][C:8]1[C:3]([O:2][CH3:1])=[CH:4][C:5]([N+:17]([O-:19])=[O:18])=[C:6]([CH:11]=[CH:12][N+:13]([O-:15])=[O:14])[N:7]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 517045Sodium AcetateHCID 59432601HCID 59432601, compound2×

Product 1

HCID 72297485HCID 72297485, compoundYield 89.2%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

Bring 1-(5,6-dimethoxy-3-nitropyridin-2-yl)-2-nitroethanol, 7 (173 mg, 0.63 mmol) and NaOAc (208 mg, 2.53 mmol) to reflux in Ac2O (5.0 mL), following the reaction by LC-MS. After 45 min, pour the reaction mixture onto an ice/H2O mixture, neutralize with NaHCO3, extract with EtOAc, wash with saturated NaHCO3, dry (MgSO4) and concentrate. Purify the raw product by flash chromatography (EtOAc at 20%/heptane) to give 8 (144 mg, 89.2%) as an ivory-colored solid, which is an 8:2 mixture of isomers: 1H NMR (CDCl3) δ 8.68 (d, 0.8 H, J=12.9 Hz), 8.57 (d, 1.6 H, J=13 Hz), 7.99 (d, 0.83 H, J=12.9 Hz), 7.72 (d, 1H, J=11.7 Hz), 7.3 (d, 0.15 H, J=12 Hz), 4.18 (s, 2.6 H), 4.15 (s, 0.56 H), is 4.05 (s, 2.8 H), 3.97 (0.54 H); Rf (EtOAc at 40%/heptane, two spots)=0.4 and 0.42; m/z obs.=256 (M+1).

Workup

  1. customthe reaction by LC-MS
  2. extractionextract with EtOAc
  3. washwash with saturated NaHCO3
  4. dry with materialdry (MgSO4)
  5. concentrationconcentrate
  6. customPurify the raw product by flash chromatography (EtOAc at 20%/heptane)

Sources & evidence

ORD record
ord-4713aa30f259428c9bca807258f8a5f9
Source dataset
uspto-grants-2010_08
Patent number
US07786114B2

Reaction notes

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