O-Toluidine → HCID 9926017、化合物

HRID 1416667ノート

反応式

HRID 1416667 の反応式
[O:1]=[C:2]1[CH:11]2[CH2:12][CH2:13]O[C:10]2=[C:9]2[C:4]([C:5]([CH3:15])=[CH:6][CH:7]=[CH:8]2)=[N:3]1.[CH3:16][C:17]1[CH:23]=[CH:22][CH:21]=[CH:20][C:18]=1[NH2:19]>C(O)COCCO>[CH3:16][C:17]1[CH:23]=[CH:22][CH:21]=[CH:20][C:18]=1[N:19]1[C:10]2[C:9]3[CH:8]=[CH:7][CH:6]=[C:5]([CH3:15])[C:4]=3[NH:3][C:2](=[O:1])[C:11]=2[CH2:12][CH2:13]1

参加物

4

反応物 2

HCID 7242O-ToluidineHCID 676261834-Oxo-6-methyl-2,3-dihydrofuro[3,2-c]quinoline

生成物 1

HCID 9926017HCID 9926017、化合物収率 81.6%

試薬・触媒・溶媒 1

HCID 8117Diethylene Glycol溶媒

反応条件

温度
250 °C

実験手順

4-Oxo-6-methyl-2,3-dihydrofuro[3,2-c]quinoline (201 mg, 1.0 mmol) was dissolved in 10 ml of diethylene glycol in a pressure tube and 2-methylaniline (267 μl, 2.5 mmol) was added under nitrogen. The reaction mixture was heated at 250° C. for 15 hours. The reaction mixture was diluted with 20 ml of saline and the aqueous layer was extracted with methylene chloride (15 ml×3). After washing with water (15 ml×3), the organic layer was dried with anhydrous magnesium sulfate and filtered, and concentrated under reduced pressure. The residue was purified with ethyl acetate as eluent by silica gel chromatography to obtain 237 mg of a desired compound as solid in 82 % of yield.

後処理

  1. additionThe reaction mixture was diluted with 20 ml of saline
  2. extractionthe aqueous layer was extracted with methylene chloride (15 ml×3)
  3. washAfter washing with water (15 ml×3)
  4. dry with materialthe organic layer was dried with anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified with ethyl acetate as eluent by silica gel chromatography

出典と根拠

ORDレコード
ord-d68d5b072fa049578cf1550cb50a176f
出典データセット
uspto-grants-1999_06
特許番号
US05914402

反応ノート

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