Methanol → HCID 67190045, compound

HRID 551817Notes

Reaction equation

HRID 551817 reaction equation
[N:1]1([C:11]2[CH:19]=[CH:18][C:14]([C:15]([OH:17])=[O:16])=[CH:13][CH:12]=2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[NH:4][CH2:3][CH2:2]1.S(=O)(=O)(O)O.[CH3:25]O>>[N:1]1([C:11]2[CH:19]=[CH:18][C:14]([C:15]([O:17][CH3:25])=[O:16])=[CH:13][CH:12]=2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[NH:4][CH2:3][CH2:2]1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 671879934-(3,4-dihydroquinoxalin-1(2H)-yl)benzoic acid

Product 1

HCID 67190045HCID 67190045, compound

Procedure

3.8 g of 4-(3,4-dihydroquinoxalin-1(2H)-yl)benzoic acid and 70 ml of methanol are introduced into a 250 ml round-bottomed flask equipped with a magnetic stirrer. 4.4 ml of 97% sulfuric acid are added dropwise and the reaction medium is stirred at ambient temperature for 18 h. The methanol is partially evaporated. The remaining solution is poured onto a water-plus-ice mixture, neutralized by slow addition of sodium hydrogencarbonate and extracted 3 times with ethyl acetate. The organic phases are combined, washed with water and with a saturated sodium chloride solution, dried over sodium sulfate and concentrated under reduced pressure. The residue is chromatographed on silica gel eluted with a gradient of ethyl acetate from 10% to 20% in heptane. 2.8 g of methyl 4-(3,4-dihydroquinoxalin-1(2H)-yl)benzoate are obtained.

Workup

  1. customequipped with a magnetic stirrer
  2. customThe methanol is partially evaporated
  3. additionThe remaining solution is poured onto a water-plus-ice mixture
  4. additionneutralized by slow addition of sodium hydrogencarbonate
  5. extractionextracted 3 times with ethyl acetate
  6. washwashed with water and with a saturated sodium chloride solution
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe residue is chromatographed on silica gel
  10. washeluted with a gradient of ethyl acetate from 10% to 20% in heptane

Sources & evidence

ORD record
ord-f602d7d35335466baf32d2ac8323da3d
Source dataset
uspto-grants-2011_05
Patent number
US07947834B2

Reaction notes

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