O-Toluidine → HCID 9926017, 화합물

HRID 1416667노트

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HRID 1416667 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

HCID 9926017HCID 9926017, 화합물수율 81.6%

시약·촉매·용매 1

HCID 8117Diethylene Glycol용매

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온도
250 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-d68d5b072fa049578cf1550cb50a176f
출처 데이터셋
uspto-grants-1999_06
특허 번호
US05914402

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