Methanol → Methyl quinoline-6-carboxylate

HRID 1404763Notes

Reaction equation

HRID 1404763 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][C:7]([C:11]([OH:13])=[O:12])=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.S(Cl)(Cl)=O.[CH3:18]O>>[N:1]1[C:10]2[C:5](=[CH:6][C:7]([C:11]([O:13][CH3:18])=[O:12])=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 825716-Quinolinecarboxylic acid

Product 1

HCID 736812Methyl quinoline-6-carboxylateYield 75%

Conditions

Temperature
65 °C

Procedure

To a solution of quinoline-6-carboxylic acid (183 g, 1.06 mol) in methanol (1 lit.), thionyl chloride (150.7 g, 1.2 mol) was added dropwise at 0° C. and then stirred at 65° C. for 12 h. The reaction mixture was concentrated and to the residue dichloromethane and aqueous sodium carbonate solutions were added. The organic layer was dried with sodium sulphate and concentrated to afford the title compound as a brown solid (150 g, 75%).

Workup

  1. concentrationThe reaction mixture was concentrated and to the residue dichloromethane and aqueous sodium carbonate solutions
  2. additionwere added
  3. dry with materialThe organic layer was dried with sodium sulphate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-0b6c5364aa5c486aaf19a439b57a2f20
Source dataset
uspto-grants-2014_12
Patent number
US08912331B2

Reaction notes

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