Dichloromethane → Methyl 6-formyl-3-methylquinoline-2-carboxylate

HRID 1604549Notes

Reaction equation

HRID 1604549 reaction equation
[OH:1][CH2:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[C:8]([C:13]([O:15][CH3:16])=[O:14])[C:7]([CH3:17])=[CH:6]2.C(N(CC)CC)C.ClCCl>O>[CH:2]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[C:8]([C:13]([O:15][CH3:16])=[O:14])[C:7]([CH3:17])=[CH:6]2)=[O:1]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 19603207Methyl 6-hydroxymethyl-3-methylquinoline-2-carboxylate

Product 1

HCID 19603457Methyl 6-formyl-3-methylquinoline-2-carboxylateYield 77.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a mixture of methyl 6-hydroxymethyl-3-methylquinoline-2-carboxylate (193 mg), triethylamine (422 mg) dimethyl sulfoxide (2 ml) and dichloromethane (2 ml) was added portionwise sulfur trioxide pyridine complex (266 mg) in water bath and the mixture was stirred for 2 hours at the same temperature. The reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with water and brine, dried over magnesium sulfate and evaporated in vacuo. The residue was purified by preparative thin-layer chromatography (n-hexane:ethyl acetate=1:1, V/V) to give methyl 6-formyl-3-methylquinoline-2-carboxylate (149 mg).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated in vacuo
  5. customThe residue was purified by preparative thin-layer chromatography (n-hexane:ethyl acetate=1:1, V/V)

Sources & evidence

ORD record
ord-8bdceb1ac4fb422f921b3ce7c2e156b6
Source dataset
uspto-grants-1999_11
Patent number
US05994368

Reaction notes

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