Sulfuric Acid → HCID 288419, compound

HRID 1868557Notes

Reaction equation

HRID 1868557 reaction equation
[CH3:1][O:2][C:3](=[O:12])[CH2:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]([CH3:11])[CH:6]=1.S(=O)(=O)(O)O.[C:18]1(C)C=CC=CC=1>Cl.C(O)C>[CH2:1]([O:2][C:3](=[O:12])[CH2:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]([CH3:11])[CH:6]=1)[CH3:18]

Participants

6

Reactant 3

HCID 1118Sulfuric AcidHCID 1140TolueneHCID 12481736Methyl (2-methylpyridin-4-yl)acetate

Product 1

HCID 288419HCID 288419, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Procedure

The mixture of (2-methyl-pyridin-4-yl)-acetic acid methyl ester and the bis adduct (20 g) was dissolved in concentrated hydrochloric acid and heated to reflux for 1 hour. The solution was cooled, diluted with toluene, and concentrated in vacuo to give the crude acid. The acid was dissolved in ethanol, treated with a catalytic amount of sulfuric acid, and heated to reflux for 3 h. The solution was cooled to room temperature and concentrated in vacuo. The residue was dissolved in ethyl acetate and washed with saturated aqueous sodium chloride solution. The mixture was filtered and the filtrate concentrated to give 14 g of the title compound as a crude oil. MS(ES): m/e (EI*) 180.1 [M+H]

Workup

  1. temperatureheated
  2. temperatureto reflux for 1 hour
  3. temperatureThe solution was cooled
  4. concentrationconcentrated in vacuo
  5. customto give the crude acid
  6. temperatureheated
  7. temperatureto reflux for 3 h
  8. concentrationconcentrated in vacuo
  9. dissolutionThe residue was dissolved in ethyl acetate
  10. washwashed with saturated aqueous sodium chloride solution
  11. filtrationThe mixture was filtered
  12. concentrationthe filtrate concentrated

Sources & evidence

ORD record
ord-d4d20f8a1a4d449a91303b8bdc049113
Source dataset
uspto-grants-2009_12
Patent number
US07635775B2

Reaction notes

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