Citric Acid → HCID 59864847, compound

HRID 2423278Notes

Reaction equation

HRID 2423278 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH:6]=[CH:7][C:8]=1[O:9][C:10]1[C:11]([N+:20]([O-:22])=[O:21])=[C:12]2[C:16](=[CH:17][CH:18]=1)[NH:15][C:14]([CH3:19])=[CH:13]2.IC.[C:31](=O)([O-])[O-].[Cs+].[Cs+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CN(C)C=O>[CH3:31][N:15]1[C:16]2[C:12](=[C:11]([N+:20]([O-:22])=[O:21])[C:10]([O:9][C:8]3[CH:7]=[CH:6][C:5]([CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])=[CH:4][C:3]=3[O:2][CH3:1])=[CH:18][CH:17]=2)[CH:13]=[C:14]1[CH3:19]

Participants

6

Reactant 4

HCID 311Citric AcidHCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 59864827HCID 59864827, compound

Product 1

HCID 59864847HCID 59864847, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a room temperature solution of 3.1 (38 mg, 0.099 mmol) and iodomethane (6.8 μL, 0.11 mmol) dissolved in N,N-dimethylformamide (1 mL) was added cesium carbonate (35 mg, 0.11 mmol). The resulting intense red solution was stirred at room temperature overnight. After 19 h, the color had dissipated to a faint pink and HPLC indicated no 3.1 remained. Several drops of aqueous 20% citric acid solution were added and the mixture partitioned between ethyl acetate and water. The separated aqueous layer was extracted again with ethyl acetate. The combined organic extracts were washed with water twice then brine. The organic separation was stirred over magnesium sulfate, filtered and the filtrate concentrated in vacuo on a rotary evaporator to afford a yellow solid. The product was used without further purification. 1H NMR (400 MHz) (CDCl3) δ 7.35 (d, J=8.8 Hz, 1H); 6.95 (s, 1H); 6.83-6.76 (m, 3H); 6.71 (s, 1H); 4.16 (q, J=9.6 Hz, 2H); 3.88 (s, 3H); 3.70 (s, 3H); 2.48 (s, 3H); 1.27 (t, J=9.6 Hz, 3H) ppm.

Workup

  1. waitAfter 19 h
  2. customthe mixture partitioned between ethyl acetate and water
  3. extractionThe separated aqueous layer was extracted again with ethyl acetate
  4. washThe combined organic extracts were washed with water twice
  5. customThe organic separation
  6. stirringwas stirred over magnesium sulfate
  7. filtrationfiltered
  8. concentrationthe filtrate concentrated in vacuo on a rotary evaporator
  9. customto afford a yellow solid
  10. customThe product was used without further purification

Sources & evidence

ORD record
ord-d786d2f25301432ea508c23a06fac9a7
Source dataset
uspto-grants-2011_06
Patent number
US07960567B2

Reaction notes

Loading…