(6-Nitro-2-phenyl-benzoxazole-7-yl)-acetonitrile → 2-Phenyl-6,8-dihydro-oxazolo[5,4-e]indol-7-one

HRID 1859059노트

반응식

HRID 1859059 반응식
[N+]([C:4]1[CH:18]=[CH:17][C:7]2[N:8]=[C:9]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[O:10][C:6]=2[C:5]=1[CH2:19][C:20]#[N:21])([O-])=O.[OH:22]S(O)(=O)=O.O>O.C(O)(=O)C.[Zn]>[C:11]1([C:9]2[O:10][C:6]3[C:7]([N:8]=2)=[CH:17][CH:18]=[C:4]2[C:5]=3[CH2:19][C:20](=[O:22])[NH:21]2)[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

참가 물질

6

반응물 2

HCID 21253439(6-Nitro-2-phenyl-benzoxazole-7-yl)-acetonitrile2회HCID 21910475Sulfuric acid hydrate (1:1)

생성물 1

HCID 212534292-Phenyl-6,8-dihydro-oxazolo[5,4-e]indol-7-one

시약·촉매·용매 3

HCID 23994Zinc촉매HCID 176Acetic Acid용매HCID 962Water용매

반응 조건

온도
100 °C

실험 절차

A solution of (6-nitro-2-phenyl-benzoxazole-7-yl)-acetonitrile (66 mg 0.23 mmol) (Starting Material 7) was suspended in concentrated H2SO4 /H2O (1/1, 2 mL)) and stirred at 100° C. for 30 min. The resulting solution was diluted with water and extracted with ethyl acetate, and the combined organic extracts were dried over anhydrous magnesium sulfate and concentrated in vacuo to give the crude acid. To a solution of the crude acid in acetic acid (3 mL) heated at reflux was added excess zinc dust (120 mg, 1.85 mmol) portionwise during thirty minutes. The mixture was filtered through a Celite® pad and washed with hot DMF. The solvent was removed in vacuo and residue was suspended and stirred for 30 minutes in 3M hydrochloric acid. The insoluble solid material was collected, washed with water, and air dried to give 2-phenyl-6,8-dihydro-oxazolo[5,4-e]indol-7-one. (Yield 17 mg, 30%).

후처리

  1. extractionextracted with ethyl acetate
  2. dry with materialthe combined organic extracts were dried over anhydrous magnesium sulfate
  3. concentrationconcentrated in vacuo
  4. customto give the crude acid
  5. temperatureat reflux
  6. filtrationThe mixture was filtered through a Celite® pad
  7. washwashed with hot DMF
  8. customThe solvent was removed in vacuo and residue
  9. stirringstirred for 30 minutes in 3M hydrochloric acid
  10. customThe insoluble solid material was collected
  11. washwashed with water, and air
  12. customdried

출처 및 근거

ORD 기록
ord-30904b1c13a741379f37d38216bb8be5
출처 데이터셋
uspto-grants-2000_11
특허 번호
US06153634

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