Nitromethane → HCID 21516013, compound

HRID 1785601Notes

Reaction equation

HRID 1785601 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[CH3:10])[CH:5]=O.C([O-])(=O)C.[NH4+].[N+:16]([CH3:19])([O-:18])=[O:17].C(OC(=O)C)(=O)C>C(O)(=O)C>[CH3:1][C:2]1[CH:3]=[C:4](/[CH:5]=[CH:19]/[N+:16]([O-:18])=[O:17])[CH:7]=[CH:8][C:9]=1[CH3:10]

Participants

6

Reactant 4

HCID 6375NitromethaneHCID 7918Acetic AnhydrideHCID 222783,4-DimethylbenzaldehydeHCID 517165Ammonium Acetate

Product 1

HCID 21516013HCID 21516013, compoundYield 66.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 3,4-dimethylbenzaldehyde (20 mL, 0.15 mol), ammonium acetate (12.5 g, 0.16 mol), glacial acetic acid (65 mL), nitromethane (34 mL, 0.63 mol), and acetic anhydride (3.0 mL, 0.032 mol) is refluxed for 2 hours. The reaction is concentrated to an oil, then dichloromethane (100 mL) is added, and the solution is washed with water (2×) and brine. The organic phase is dried (MgSO4), and concentrated to a dark green solid. This material is re-crystallized (treated with Darco) from 50% cyclohexane/hexanes to afford 17.6 g (66% yield) of the desired compound. 1H NMR (CDCl3) δ 8.08 (dd, J=2.4 Hz, 13.5 Hz, 1H), 7.61 (dd, J=2.4 Hz, 13.5 Hz, 1H), 7.31-7.36 (m, 2H), 7.25 (d, J=7.8 Hz, 1H), 2.36 (s, 3H), 2.35 (s, 3H); MS 329 (MH+).

Workup

  1. concentrationThe reaction is concentrated to an oil
  2. additiondichloromethane (100 mL) is added
  3. washthe solution is washed with water (2×) and brine
  4. dry with materialThe organic phase is dried (MgSO4)
  5. concentrationconcentrated to a dark green solid
  6. customThis material is re-crystallized
  7. addition(treated with Darco) from 50% cyclohexane/hexanes

Sources & evidence

ORD record
ord-0174edb295e24aa8bb39b70d6165f0c0
Source dataset
uspto-grants-2009_03
Patent number
US07504517B2

Reaction notes

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