Trifluoroacetic acid → 5-(4-Nitro-benzyl)-1,3-dihydro-indol-2-one

HRID 2352778

반응식

HRID 2352778 반응식
FC(F)(F)C(O)=O.[BH4-].[Na+].[N+:10]([C:13]1[CH:30]=[CH:29][C:16]([C:17]([C:19]2[CH:20]=[C:21]3[C:25](=[CH:26][CH:27]=2)[NH:24][C:23](=[O:28])[CH2:22]3)=O)=[CH:15][CH:14]=1)([O-:12])=[O:11]>>[N+:10]([C:13]1[CH:14]=[CH:15][C:16]([CH2:17][C:19]2[CH:20]=[C:21]3[C:25](=[CH:26][CH:27]=2)[NH:24][C:23](=[O:28])[CH2:22]3)=[CH:29][CH:30]=1)([O-:12])=[O:11]

참가 물질

4

반응물 3

HCID 6422Trifluoroacetic acidHCID 4311764Sodium borohydrideHCID 687007145-(4-Nitro-benzoyl)-1,3-dihydro-indol-2-one

생성물 1

HCID 687018775-(4-Nitro-benzyl)-1,3-dihydro-indol-2-one수율 61%

실험 절차

In a dried 250 mL round bottom flask, 20.73 mL of trifluoroacetic acid was added and then cooled to 0° C. under Ar(g). NaBH4 in pellet form (1.35 g, 35.71 mmol, ˜1.5 pellets) was added to the flask. 5-(4-Nitro-benzoyl)-1,3-dihydro-indol-2-one (as prepared in Example 7, 1.0 g, 3.55 mmol) was then added in slowly over 15 min. After the addition was completed, the reaction was allowed to warm to room temperature and was stirred for 36 hours forming a yellow foamy mixture. The mixture was poured over ice-water and allowed to warm to room temperature, during which a tan solid precipitated out of solution. The tan solid was collected by filtration and washed with water affording 5-(4-Nitro-benzyl)-1,3-dihydro-indol-2-one in 61% yield (0.589 g, 2.165 mmol).

후처리

  1. additionAfter the addition
  2. customforming a yellow foamy mixture
  3. temperatureto warm to room temperature, during which a tan solid
  4. customprecipitated out of solution
  5. filtrationThe tan solid was collected by filtration
  6. washwashed with water

출처 및 근거

ORD 기록
ord-5a27ecb47f3b4eb783370ed8f2280656
출처 데이터셋
uspto-grants-2010_07
특허 번호
US07749530B2

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