Methanol → HCID 12021304, compound

HRID 1294702Notes

Reaction equation

HRID 1294702 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([CH2:11][C:12]([OH:14])=[O:13])[CH:9]=2)[CH:4]=[CH:3][CH:2]=1.O=S(Cl)Cl.[CH3:19]O>CN(C)C=O>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([CH2:11][C:12]([O:14][CH3:19])=[O:13])[CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 18675903(Quinolin-7-yl)acetic acid

Product 1

HCID 12021304HCID 12021304, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideCatalyst

Procedure

To a solution of example 11A (1.98 g, 10.59 mmol) in 40 mL of anhydrous methanol was slowly added SOCl2 (1.5 mL, 31.7 mmol), and a drop of dimethylformamide as catalyst. The mixture was refluxed for 5 hrs and then concentrated under reduced pressure. The residue was dissolved in water (10 mL) and neutralized with aqueous sodium bicarbonate to pH 8. The product was extracted with methylene chloride, dried with anhydrous sodium sulfate and concentrated under reduced pressure to afford 2.13 g of the title compound. MS (ESI+) m/z 202 (M+H)+.

Workup

  1. temperatureThe mixture was refluxed for 5 hrs
  2. concentrationconcentrated under reduced pressure
  3. dissolutionThe residue was dissolved in water (10 mL)
  4. extractionThe product was extracted with methylene chloride
  5. dry with materialdried with anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-27995b58fe0d42b6ae981bb298cddc14
Source dataset
uspto-grants-2007_07
Patent number
US07241776B2

Reaction notes

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