Methanol → methyl 2-methylquinoline-6-carboxylate

HRID 1088454Notes

Reaction equation

HRID 1088454 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[N:10]=[C:9]([CH3:14])[CH:8]=[CH:7]2)([OH:3])=[O:2].OS(O)(=O)=O.[CH3:20]O>>[C:1]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[N:10]=[C:9]([CH3:14])[CH:8]=[CH:7]2)([O:3][CH3:20])=[O:2]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 6044832-Methylquinoline-6-carboxylic acid

Product 1

HCID 2308822methyl 2-methylquinoline-6-carboxylate

Procedure

To a solution of 6-carboxy-2-methyl quinoline in MeOH (600 ml) was added concentrated H2SO4 and stirred for 3 days at room temperature. The reaction mixture was evaporated and the residue was diluted with H2O (250 ml) and ethyl acetate (250 ml), and transferred to a separatory funnel. A solution of saturated sodium bicarbonate in water (1 L) was added and extraction with ethyl acetate afforded a purple solid which was chromatographed on column of flash silica gel using hexane-ethyl acetate (2:1) as eluant to provide the title compound as a yellow solid: m.p. 98-101° C.

Workup

  1. customThe reaction mixture was evaporated
  2. additionthe residue was diluted with H2O (250 ml) and ethyl acetate (250 ml)
  3. customtransferred to a separatory funnel
  4. additionA solution of saturated sodium bicarbonate in water (1 L) was added
  5. extractionextraction with ethyl acetate
  6. customafforded a purple solid which
  7. customwas chromatographed on column of flash silica gel

Sources & evidence

ORD record
ord-59e13b04bf2f4c659c6e5790cb7a168c
Source dataset
uspto-grants-1990_10
Patent number
US04962203

Reaction notes

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