Acetic Anhydride → 2-Acetoxymethyl-5-methyl-2,3,6,7-tetrahydrofuro-[2,3-f]quinoline-7-one

HRID 1900718

반응식

HRID 1900718 반응식
[OH:1][CH2:2][CH:3]1[O:17][C:6]2=[C:7]3[C:12](=[C:13]([CH3:15])[CH:14]=[C:5]2[CH2:4]1)[NH:11][C:10](=[O:16])[CH:9]=[CH:8]3.[C:18](OC(=O)C)(=[O:20])[CH3:19]>N1C=CC=CC=1>[C:18]([O:1][CH2:2][CH:3]1[O:17][C:6]2=[C:7]3[C:12](=[C:13]([CH3:15])[CH:14]=[C:5]2[CH2:4]1)[NH:11][C:10](=[O:16])[CH:9]=[CH:8]3)(=[O:20])[CH3:19]

참가 물질

4

반응물 2

HCID 7918Acetic AnhydrideHCID 233696792-Hydroxymethyl-5-methyl-2,3,6,7-tetrahydrofuro[2,3-f]quinoline-7-one

생성물 1

HCID 233695822-Acetoxymethyl-5-methyl-2,3,6,7-tetrahydrofuro-[2,3-f]quinoline-7-one수율 80.1%

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

To a solution of 2-hydroxymethyl-5-methyl-2,3,6,7-tetrahydrofuro[2,3-f]quinoline-7-one (261 mg) in anhydrous pyridine (7 ml), acetic anhydride (233 mg) was added. The mixture was stirred at room temperature for 1 hour, and further stirred at 50° C. for 1 hour. After completion of the reaction, the solvent was distilled off, and the residue was dissolved in chloroform, and washed with water. After drying, the solvent was distilled off to obtain 305 mg of a crude product. The crude product was purified by silica gel column chromatography (eluent=chloroform:methanol=70:1) to obtain 247 mg of a target product (80.0%). The product was recrystallized from chloroform-n-hexane, and as a result, colorless powdery crystals were obtained (mp. 197°-200° C.).

후처리

  1. stirringfurther stirred at 50° C. for 1 hour
  2. customAfter completion of the reaction
  3. distillationthe solvent was distilled off
  4. dissolutionthe residue was dissolved in chloroform
  5. washwashed with water
  6. customAfter drying
  7. distillationthe solvent was distilled off
  8. customto obtain 305 mg of a crude product
  9. customThe crude product was purified by silica gel column chromatography (eluent=chloroform:methanol=70:1)

출처 및 근거

ORD 기록
ord-1f4dbe820cff407fa09690a870f26264
출처 데이터셋
uspto-grants-1996_11
특허 번호
US05576324

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