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

HRID 1604549ノート

反応式

HRID 1604549 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

HCID 19603457Methyl 6-formyl-3-methylquinoline-2-carboxylate収率 77.9%

試薬・触媒・溶媒 1

HCID 962Water溶媒2 回

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-8bdceb1ac4fb422f921b3ce7c2e156b6
出典データセット
uspto-grants-1999_11
特許番号
US05994368

反応ノート

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