Methanol → methyl quinoline-3-carboxylate

HRID 587869Notes

Reaction equation

HRID 587869 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]([C:11]([OH:13])=[O:12])[CH:2]=1.S(Cl)(Cl)=O.[CH3:18]O>>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]([C:11]([O:13][CH3:18])=[O:12])[CH:2]=1

Participants

4

Reactant 3

HCID 887Methanol2×HCID 24386Thionyl ChlorideHCID 80971Quinoline-3-carboxylic acid

Product 1

HCID 257955methyl quinoline-3-carboxylateYield 99%

Conditions

Temperature
80 °C

Procedure

The solution of quinoline-3-carboxylic acid (3 g, 17.32 mmol) in methanol (30 mL) was cooled on ice bath at 0° C. Then thionyl chloride (1.264 mL, 17.32 mmol) was added and the reaction mixture was heated to 80° C. and maintained overnight. Reaction was monitored by TLC. After completion of reaction methanol was evaporated under reduced pressure and the resultant residue was basified with saturated sodium bicarbonate to make pH (7 to 8) to get white solid which was filtered and dried to get methyl quinoline-3-carboxylate (3.2 g, yield-99%) as a white solid; m/z-187.3.

Workup

  1. temperaturemaintained overnight
  2. customReaction
  3. customwas evaporated under reduced pressure
  4. customto get white solid which
  5. filtrationwas filtered
  6. customdried

Sources & evidence

ORD record
ord-a56325cae9d242099af622a1cc532b81
Source dataset
uspto-grants-2016_01
Patent number
US09227919B2

Reaction notes

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