Methanol → HCID 22990129, compound

HRID 1169363Notes

Reaction equation

HRID 1169363 reaction equation
[NH2:1][C:2]1[CH:9]=[C:8]([C:10]2[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=2)[CH:7]=[CH:6][C:3]=1C=O.[C:17]([OH:22])(=[O:21])[C:18]([CH3:20])=O.[OH-].[Na+].[CH3:25]O>>[CH3:16][C:13]1[CH:12]=[CH:11][C:10]([C:8]2[C:9]3[C:2](=[CH:3][CH:6]=[CH:7][CH:25]=3)[N:1]=[C:18]([C:17]([OH:22])=[O:21])[CH:20]=2)=[CH:15][CH:14]=1

Participants

5

Reactant 4

HCID 887Methanol2×HCID 1060Pyruvic AcidHCID 14798Sodium HydroxideHCID 22990101HCID 22990101, compound

Product 1

HCID 22990129HCID 22990129, compound

Conditions

Temperature
55 °C

Procedure

Into a solution of 2-amino-4-(4-methylphenyl)benzaldehyde (0.23 g) and pyruvic acid (192 mg) in methanol (20 ml) was added a solution of sodium hydroxide (349 mg)/methanol (20 ml), and the resulting mixture was stirred at 50-60° C. for 9 hours and was then concentrated. The concentrate was extracted with water, and the aqueous layer was washed twice with diethyl ether and was then mixed with 1 N hydrochloric acid to adjust the pH to 1-2. The resulting mixture was extracted with ethyl acetate, and the extract was washed with an aqueous solution of sodium chloride. The extract was dried (anhydrous magnesium sulfate) and was then concentrated. The residue was subjected to purification using silica gel column chromatography (ethyl acetate/methanol=4/1) to obtain 4-(4-methylphenyl)quinoline-2-carboxylic acid (117 mg) as an orange powder.

Workup

  1. concentrationwas then concentrated
  2. extractionThe concentrate was extracted with water
  3. washthe aqueous layer was washed twice with diethyl ether
  4. additionwas then mixed with 1 N hydrochloric acid
  5. extractionThe resulting mixture was extracted with ethyl acetate
  6. washthe extract was washed with an aqueous solution of sodium chloride
  7. dry with materialThe extract was dried (anhydrous magnesium sulfate)
  8. concentrationwas then concentrated
  9. customThe residue was subjected to purification

Sources & evidence

ORD record
ord-23bf8a974af24129825aec69cc89eed8
Source dataset
uspto-grants-2003_09
Patent number
US06627651B1

Reaction notes

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